N-(1,2,5-oxadiazol-3-yl)-, n-(tetrazol-5-yl)- and n-(triazol-5-yl)bicycloarylcarboxamides and their use as herbicides

ABSTRACT

N-(1,2,5-Oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)bicycloarylcarboxamides of the general formula (I) are described as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), R 3 , R 4  and R 5  are each radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is a heterocycle. X and Y are each oxygen and sulfur.

The invention relates to the technical field of herbicides, especially that of herbicides for selective control of broad-leaved weeds and weed grasses in crops of useful plants.

WO2003/010143 and WO2003/010153 disclose particular N-(tetrazol-5-yl)- and N-(triazol-5-yl)benzamides and the pharmacological action thereof. Under CAS No. 639048-78-5, the compound N-(1-propyltetrazol-5-yl)-2,5-dichlorobenzamide is known. No herbicidal action of these compounds is disclosed in these documents. European patent applications No. 0912169.0 and No. 10174893.7, which have earlier priority dates but were yet to be published at the priority date of the present application, disclose N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides and the use thereof as herbicides.

It has now been found that N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)bicycloarylcarboxamides are of good suitability as herbicides.

The present invention thus provides N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloarylcarboxamides of the formula (I) or salts thereof

in which Q is a Q1, Q2 or Q3 radical,

R¹ is (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₂-C₆)-alkenyl, (C₁-C₆)-alkoxy-(C₂-C₆)-alkynyl, CH₂R⁶, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by u radicals from the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl; R² is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy, halo-(C₂-C₆)-alkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or phenyl each substituted by u radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen; R³ and R⁴ are each independently hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, (C₃-C₇)-halocycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro or cyano; R⁵ is hydrogen or fluorine; R⁶ is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C₃-C₆)-cycloalkyl, or heteroaryl, heterocyclyl or phenyl each substituted by u radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen; R⁷ and R⁸ are each independently hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, halo-(C₃-C₇)-cycloalkyl, —OR⁹, S(O)_(m)R⁹, (C₁-C₆)-alkylthio, halo-(C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, halo-(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, halo-(C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro, cyano, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by u radicals from the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, or R⁷ and R⁸ together with the carbon atom to which they are bonded form the —X¹—(CH₂)_(r)—X²—, —(CH₂)_(s)—X³—, —(CH₂)_(t)—X³—CH₂—, —(CH₂)_(v)—X³—CH₂CH₂— or —(CH₂)_(w)— unit in which each of the (CH₂) groups is substituted by m radicals from the group consisting of halogen, methyl and (C₁-C₃)-alkoxy, or R⁷ and R⁸ together with the carbon atom to which they are bonded form the —O—N((C₁-C₃)-alkyl)-CHR¹⁰—CH₂— or —O—N═CR¹⁰—CH₂— unit in which each of the (CH₂) groups is substituted by m radicals from the group consisting of halogen and methyl; R⁹ is hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, (C₃-C₇)-halocycloalkyl, (C₃-C₇)-cycloalkyl-(C₁-C₃)-alkyl, halo-(C₃-C₇)-cycloalkyl-(C₁-C₃)-alkyl, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl; R¹⁰ is hydrogen, (C₁-C₃)-alkyl, or phenyl substituted by u radicals from the group consisting of (C₁-C₃)-alkyl, halogen, cyano and nitro; R¹¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, formyl, (C₂-C₆)-alkylcarbonyl, (C₂-C₆)-alkoxycarbonyl or (C₁-C₂)-alkylsulfonyl; X and Y are each independently O, S, SO, SO₂, C═O, C═S, NR¹⁰, CR⁷R⁸, C═NOR¹⁰ or C═NN(R¹¹)₂; X¹ and X² are each independently O, S or N((C₁-C₃)-alkyl);

X³ is O or S;

m is 0, 1 or 2; n is 1, 2 or 3; r is 2, 3 or 4; s is 2, 3, 4 or 5; t is 1, 2, 3 or 4; u is 0, 1, 2 or 3; v is 2 or 3; w is 2, 3, 4, 5 or 6.

In the formula (I) and all the formulae which follow, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or isopropyl, n-, iso-, tert- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, semisaturated or fully unsaturated cyclic radical containing 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl,

Heteroaryl is an aromatic cyclic radical containing 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

When a group is polysubstituted by radicals, this means that this group is substituted by one or more identical or different radicals from those mentioned.

According to the nature and the bonding of the substituents, the compounds of the general formula (I) may be present as stereoisomers. When, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers likewise occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. It is equally possible to selectively prepare stereoisomers by using stereoselective reactions using optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof which are encompassed by the general formula (I) but not defined specifically.

Preference is given to compounds of the general formula (I) in which

R¹ is (C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, halo-(C₁-C₃)-alkyl or (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl; R² is hydrogen, (C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, halo-(C₁-C₃)-alkyl, (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, methoxycarbonyl, ethoxycarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl or methoxymethyl; R³ and R⁴ are each independently hydrogen, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro or cyano; R⁵ is hydrogen; R⁷ and R⁸ are each independently hydrogen, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, —OR⁹, —S(O)_(m)R⁹, (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl, (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl, halogen, nitro, cyano, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by u radicals from the group consisting of halogen, nitro, cyano, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl, (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy and (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl, or R⁷ and R⁸ together with the carbon atom to which they are bonded form the —X¹—(CH₂)_(r)—X²—, —(CH₂)_(s)—X³—, —(CH₂)_(t)—X³—CH₂—, —(CH₂)_(v)—X³—(CH₂CH₂— or —(CH₂)_(w)— unit in which each of the (CH₂) groups is substituted by m radicals from the group consisting of halogen, methyl and (C₁-C₃)-alkoxy, or R⁷ and R⁸ together with the carbon atom to which they are bonded form the —O—N((C₁-C₃)-alkyl)-CHR¹⁰—(CH₂— or —O—N═CR¹⁰—(CH₂— unit in which each of the (CH₂) groups is substituted by m radicals from the group consisting of halogen and methyl; R⁹ is hydrogen, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₂-C₃)-alkenyl, (C₂-C₄)-alkynyl, (C₃-C₅)-cycloalkyl, (C₃-C₅)-cycloalkyl-(C₁-C₃)-alkyl, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl, (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy and (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl; R¹⁰ is hydrogen or (C₁-C₃)-alkyl; X and Y are each independently O, SO₂, C═O, C═S, CR⁷R⁸, C═NOR¹⁰; X¹ and X² are each independently O, S, N(CH₃);

X³ is O or S;

m is 0, 1 or 2; n is 1 or 2; r is 2 or 3; s is 2, 3 or 4; t is 1, 2 or 3; u is 0, 1 or 2; v is 2 or 3; w is 2, 3, 4 or 5.

In all the formulae specified hereinafter, the substituents and symbols have the same definition as in formula (I), unless defined differently.

Inventive compounds in which Q is Q1 or Q2 can be prepared, for example, by the method shown in scheme 1, by base-catalyzed reaction of a bicyclic benzoyl chloride (II) with a 5-amino-1H-1,2,4-triazole or 5-amino-1H-tetrazole (III):

B therein is CH or N. The bicyclic benzoyl chlorides of the formula (II) or their parent bicyclic benzoic acids are known in principle and can be prepared, for example, by the methods known in WO 96/25413, WO 97/09324, WO 97/30993, WO 97/08164, WO 98/49159, WO 98/35954, WO 98/12192, WO 0014087 and EP 0636622.

Inventive compounds in which Q is Q1 or Q2 can also be prepared by the method shown in scheme 2, by reaction of a benzoic acid of the formula (IV) with a 5-amino-1H-1,2,4-triazole or 5-amino-1H-tetrazole (III):

For the activation, it is possible to use dehydrating reagents which are typically used for amidation reactions, for example 1,1′-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc.

Inventive compounds in which Q is Q1 or Q2 can also be prepared by the method shown in scheme 3, by reaction of an N-(1H-1,2,4-triazol-5-yl)benzamide, N-(1H-tetrazol-5-yl)benzamide, N-(1H-1,2,4-triazol-5-yl)nicotinamide or N-(1H-tetrazol-5-yl)nicotinamide:

For this reaction shown in scheme 3, it is possible, for example, to use alkylating agents, for example alkyl halides or sulfonates or dialkyl sulfates, in the presence of a base.

It may be appropriate to alter the sequence of reaction steps. For instance, benzoic acids bearing a sulfoxide cannot be converted directly to their acid chlorides. One option here is first to prepare the amide to the thioether stage and then to oxidize the thioether to the sulfoxide.

The 5-amino-1H-tetrazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature. For example, substituted 5-aminotetrazoles can be prepared from aminotetrazole by the method described in Journal of the American Chemical Society (1954), 76, 923-924:

In the above reaction, X is a leaving group such as iodine. Substituted 5-aminotetrazoles can also be synthesized, for example, as described in Journal of the American Chemical Society (1954) 76, 88-89:

The 5-amino-1H-triazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature. For example, substituted 5-aminotriazoles can be prepared from aminotriazole by the method described in Zeitschrift füer Chemie (1990), 30(12), 436-437:

Substituted 5-aminotriazoles can also be synthesized, for example, as described in Chemische Berichte (1964), 97(2), 396-404:

Substituted 5-aminotriazoles can also be synthesized, for example, as described in Angewandte Chemie (1963), 75, 918:

Inventive compounds in which Q is Q3 can be prepared, for example, by the method shown in scheme 4, by base-catalyzed reaction of a bicyclic benzoyl chloride (II) with a 4-amino-1,2,5-oxadiazole (VI):

Inventive compounds can also be prepared by the method described in scheme 5, by reacting a bicyclic benzoic acid of the formula (IV) with a 4-amino-1,2,5-oxadiazole (VI):

For the activation, it is possible to use dehydrating reagents which are typically used for amidation reactions, for example 1,1′-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc.

The 4-amino-1,2,5-oxadiazoles of the formula (VI) are either commercially available or known, or can be prepared analogously to methods known from the literature. For example, 3-alkyl-4-amino-1,2,5-oxadiazoles can be prepared from β-keto esters by the method described in Russian Chemical Bulletin, Int. Ed., vol. 54, 4, p. 1032-1037 (2005):

3-Aryl-4-amino-1,2,5-oxadiazoles can be synthesized, for example, as described in Russian Chemical Bulletin, 54(4), 1057-1059, (2005) or Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 26B(7), 690-2, (1987):

3-Amino-4-halo-1,2,5-oxadiazoles can be prepared, for example, by a Sandmeyer reaction from the commercially available 3,4-diamino-1,2,5-oxadiazole by the method described in Heteroatom Chemistry 15(3), 199-207 (2004):

Nucleophilic R² radicals can be introduced into 3-amino-1,2,5-oxadiazoles by substitution of the leaving group L as described in Journal of Chemical Research, Synopses, (6), 190, 1985 or in or Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, (9), 2086-8, 1986 or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3), 596-614, 2004:

Collections of compounds of the formula (I) and/or salts thereof which can be synthesized by the abovementioned reactions can also be prepared in a parallelized manner, in which case this may be accomplished in a manual, partly automated or fully automated manner. It is possible, for example, to automate the conduct of the reaction, the workup or the purification of the products and/or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (editor: Günther Jung), Wiley, 1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possible to use a number of commercially available instruments, for example Calypso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, England, or MuItiPROBE Automated Workstations from Perkin Elmer, Waltham, Mass. 02451, USA. For the parallelized purification of compounds of the general formula (I) and salts thereof or of intermediates which occur in the course of preparation, available apparatuses include chromatography apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which the individual working steps are automated, but manual operations have to be carried out between the working steps. This can be circumvented by using partly or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be purchased, for example, from Caliper, Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can be supported by the use of polymer-supported reagents/scavenger resins. The technical literature describes a number of experimental protocols, for example ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

Aside from the methods described here, the compounds of the general formula (I) and salts thereof can be prepared completely or partially by solid-phase supported methods. For this purpose, individual intermediates or all intermediates in the synthesis or a synthesis adapted for the corresponding procedure are bound to a synthesis resin. Solid-phase supported synthesis methods are described adequately in the technical literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (editor: Günther Jung), Wiley, 1999. The use of solid-phase-supported synthesis methods permits a number of protocols known from the literature, and these may again be executed manually or in an automated manner. The reactions can be performed, for example, by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Either on a solid phase or in the liquid phase, the performance of single or multiple synthesis steps can be supported by the use of microwave technology. The technical literature describes a number of experimental protocols, for example Microwaves in Organic and Medicinal Chemistry (editors: C. O. Kappe and A. Stadler), Wiley, 2005.

The preparation by the process described here gives compounds of the formula (I) and salts thereof in the form of substance collections, which are called libraries. The present invention also provides libraries comprising at least two compounds of the formula (I) and salts thereof.

The inventive compounds of the formula (I) (and/or salts thereof), collectively referred to hereinafter as “inventive compounds”, have excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active ingredients also have good control over perennial weed plants which are difficult to control and produce shoots from rhizomes, root stocks or other perennial organs.

The present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, in which one or more inventive compound(s) is/are applied to the plants (for example weed plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), to the seeds (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation). The inventive compounds can be deployed, for example, prior to sowing (if appropriate also by incorporation into the soil), prior to emergence or after emergence. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the inventive compounds are as follows, though the enumeration is not intended to impose a restriction to particular species:

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the inventive compounds are applied to the soil surface before germination, either the weed seedlings are prevented completely from emerging or the weeds grow until they have reached the cotyledon stage, but then stop growing and, eventually, after three to four weeks have passed, die completely.

If the active ingredients are applied post-emergence to the green parts of the plants, there is likewise stoppage of growth after the treatment, and the harmful plants remain at the growth stage of the time of application, or they die completely after a certain time, such that competition by the weeds, which is harmful to the crop plants, is thus eliminated very early and in a lasting manner.

Although the inventive compounds have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, are damaged only to an insignificant extent, if at all, depending on the structure of the respective inventive compound and the application rate thereof. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamentals.

In addition, the inventive compounds (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plant's own metabolism with a regulatory effect, and can thus be used to control plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. In addition, they are also suitable for general control and inhibition of unwanted vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role for many monocotyledonous and dicotyledonous crops, since, for example, this can reduce or completely prevent lodging.

By virtue of their herbicidal and plant growth-regulating properties, the active ingredients can also be used for control of harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are notable for special advantageous properties, for example for resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or organisms that cause plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or with a different fatty acid composition in the harvested material.

With regard to transgenic crops, preference is given to the use of the inventive compounds in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet/sorghum, rice and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables. Preferably, the inventive compounds can be used as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

Preference is given to the use of the inventive compounds or salts thereof in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet/sorghum, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables. Preferably, the inventive compounds can be used as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional breeding methods and the generation of mutants. Alternatively, novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, there have been many descriptions of:

-   -   recombinant modifications of crop plants for the purpose of         modifying the starch synthesized in the plants (e.g. WO         92/11376, WO 92/14827, WO 91/19806),     -   transgenic crop plants which are resistant to particular         herbicides of the glufosinate type (cf., for example,         EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or         the sulfonylureas (EP-A-0257993, US-A-5013659),     -   transgenic crop plants, for example cotton, with the ability to         produce Bacillus thuringiensis toxins (Bt toxins) which make the         plants resistant to particular pests (EP-A-0142924,         EP-A-0193259),     -   transgenic crop plants with a modified fatty acid composition         (WO 91/13972),     -   genetically modified crop plants with novel constituents or         secondary metabolites, for example novel phytoalexins, which         cause an increased disease resistance (EPA 309862, EPA0464461),     -   genetically modified plants with reduced photorespiration, which         have higher yields and higher stress tolerance (EPA 0305398),     -   transgenic crop plants which produce pharmaceutically or         diagnostically important proteins (“molecular pharming”),     -   transgenic crop plants which are notable for higher yields or         better quality,     -   transgenic crop plants which are notable for a combination, for         example, of the abovementioned novel properties (“gene         stacking”).

Numerous molecular biology techniques which can be used to produce novel transgenic plants with modified properties are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.), Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or Christou, “Trends in Plant Science” 1 (1996) 423-431).

For such recombinant manipulations, nucleic acid molecules which allow mutagenesis or a sequence change by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it it possible, for example, to undertake base exchanges, remove parts of sequences or add natural or synthetic sequences. For the connection of the DNA fragments to one another, it is possible to add adapters or linkers to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene and Klone”, VCH Weinheim, 2nd edition, 1996.

The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one appropriate antisense RNA, or of a sense RNA for achievement of a cosuppression effect, or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product. For this purpose, it is firstly possible to use DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequences present, or else DNA molecules which comprise only parts of the coding sequence, in which case these parts must be long enough to bring about an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.

When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, in order to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give whole plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants.

Thus, it is possible to obtain transgenic plants whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences, or expression of heterologous (=foreign) genes or gene sequences.

Preferably, the inventive compounds can be used in transgenic crops which are resistant to growth regulators, for example dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.

On employment of the inventive active ingredients in transgenic crops, not only do the effects toward weed plants observed in other crops occur, but often also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

The invention therefore also provides for the use of the inventive compounds as herbicides for control of harmful plants in transgenic crop plants.

The inventive compounds can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise the inventive compounds.

The inventive compounds can be formulated in various ways, according to the biological and/or physicochemical parameters required. Examples of possible formulations include: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), seed-dressing products, granules for broadcasting and soil application, granules (GR) in the form of microgranules, sprayable granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition 1986, Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary formulation assistants, such as inert materials, surfactants, solvents and further additives are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J., Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tankmix. Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active ingredient, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′ dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate. To produce the wettable powders, the herbicidal active ingredients are ground finely, for example in customary apparatus such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation assistants.

Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). The emulsifiers used may, for example, be: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active ingredient with finely distributed solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They can be produced, for example, by wet grinding by means of commercial bead mills with optional addition of surfactants as already listed above, for example, for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.

Granules can be produced either by spraying the active ingredient onto adsorptive granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carrier substances, such as sand, kaolinites or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers.

Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

For the production of pan granules, fluidized bed granules, extruder granules and spray granules, see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th ed., McGraw-Hill, New York 1973, p. 8-57.

For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally 0.1 to 99% by weight, especially 0.1 to 95% by weight, of inventive compounds.

In wettable powders, the active ingredient concentration is, for example, about 10 to 90% by weight; the remainder to 100% by weight consists of the customary formulation constituents. In emulsifiable concentrates, the active ingredient concentration may be about 1 to 90% and preferably 5 to 80% by weight.

Formulations in the form of dusts comprise 1 to 30% by weight of active ingredient, preferably usually 5 to 20% by weight of active ingredient; sprayable solutions contain about 0.05 to 80% and preferably 2 to 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends partly on whether the active compound is present in liquid or solid form and on which granulation assistants, fillers, etc., are used. In the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active ingredient formulations mentioned optionally comprise the respective customary tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity.

On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tankmix.

Usable combination partners for the inventive compounds in mixture formulations or in a tankmix are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2009 and literature cited therein. Examples of known herbicides or plant growth regulators which can be combined with the inventive compounds include the active ingredients which follow (the compounds are designated by the “common name” according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always encompass all use forms, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. In this list, one or else, in some cases, more than one application form is mentioned by way of example:

acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryne, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlortoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, inabenfide, indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazasulfuron, methazole, methiopyrsulfuron, methiozolin, methoxyphenone, methyldymron, 1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogensulfate, monolinuron, monosulfuron, monosulfuron ester, monuron, MT-128, i.e. 6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazine-3-amine, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolate-sodium (isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazole, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, i.e. methyl (2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate, sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryne, thenylchlor, thiafluamide, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

For application, the formulations in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type formulations, granules for soil application or granules for broadcasting and sprayable solutions are not normally diluted further with other inert substances prior to application.

The required application rate of the compounds of the formula (I) varies with the external conditions, including temperature, humidity and the type of herbicide used. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha or more active substance, but it is preferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES 1. Synthesis of 4-chloro-3-methoxy-N-(4-methyl-1,2,5-oxadiazol-3-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide 1,1-dioxide (table example No. 1928)

1.00 g (3.14 mmol) of 4-chloro-3-methoxy-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide and 0.33 g (3.15 mmol) of 4-methyl-1,2,5-oxadiazol-3-yl-amine were dissolved at room temperature (RT) in 35 ml of CH₂Cl₂, 3.02 g (4.74 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) were added and the mixture was stirred at RT for 1 h. Subsequently, 2.18 ml (15.64 mmol) of triethylamine and 75 mg (0.61 mmol) of 4-dimethylaminopyridine (DMAP) were added and the whole mixture was stirred at RT for 16 h. This was followed by washing with water and twice with 6N hydrochloric acid, drying of the organic phase over Na₂SO₄ and filtration with suction through silica gel, washing through with 1:2 heptane/ethyl acetate and concentration. Yield 708 mg (63%).

¹H NMR (CDCl₃): δ=2.44 (s, 3H), 3.53 (s, 3H), 3.57 (dd, 1H), 3.71 (d, 1H), 5.15 (d, 1H), 7.55 (d, 1H), 7.74 (d, 1H), 9.40 (s, 1H)

2. Synthesis of 4-chloro-N-(1-methyl-1H-1,2,4-triazol-5-yl)-2,3-dihydro-1-benzothiophen-5-carboxamide 1,1-dioxide (table example No. 1545)

0.80 g (3.24 mmol) of 4-chloro-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide, 0.72 g (2.43 mmol) of di(1-methyl-1H-1,2,4-triazol-5-amine) sulfate and 20 mg (0.164 mmol) of DMAP were initially charged in 5 ml of pyridine, 0.65 g (5.35 mmol) of thionyl chloride were added and the mixture was stirred at 70° C. for 1 h. Subsequently, 0.5 ml of water was added, and the mixture was stirred for a further 30 min, acidified with saturated KHSO₄ solution and extracted three times with 100 ml each time of ethyl acetate. The combined organic phases were washed with saturated NaHCO₃ solution, dried over Na₂SO₄ and concentrated. The residue was purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 642 mg (61%).

¹H NMR (DMSO-d₆): δ=3.40 (t, 2H), 3.74 (t, 2H), 3.79 (s, 3H), 7.89 (br, 3H), 11.39 (s, 1H)

3. Synthesis of N-(1-ethyl-1H-tetrazol-5-yl)-4,4,5,8-tetramethyl-3,4-dihydro-2H-thiochromene-6-carboxamide 1,1-dioxide (table example No. 189)

1.00 g (3.54 mmol) of 4,4,5,8-tetramethyl-3,4-dihydro-2H-thiochromene-6-carboxylic acid 1,1-dioxide, 0.63 g (5.32 mmol) of 1-ethyl-5-aminotetrazole and 23 mg (0.188 mmol) of DMAP were initially charged in 7 ml of pyridine, 0.71 g (5.86 mmol) of thionyl chloride were added and the mixture was stirred at 70° C. for 1 h.

Subsequently, 0.5 ml of water was added, and the mixture was stirred for a further 30 min, acidified with saturated KHSO₄ solution and extracted three times with 100 ml each time of ethyl acetate. The combined organic phases were washed with saturated NaHCO₃ solution, dried over Na₂SO₄ and concentrated. The residue was purified by column chromatography (silica gel, heptane/ethyl acetate). Yield 492 mg (37%).

¹H NMR (CDCl₃): δ=1.56 (s, 6H), 1.64 (t, 3H), 2.36 (dd, 2H), 2.65 (s, 3H), 2.77 (s, 3H), 3.43 (dd, 2H), 4.46 (q, 2H), 7.37 (s, 3H), 10.16 (s, 1H)

The examples listed in the tables below were prepared analogously to the abovementioned methods or are obtainable analogously to the abovementioned methods. The compounds listed in the tables below are very particularly preferred.

The abbreviations used mean:

Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl Ph = phenyl

TABLE 1 Inventive compounds of the general formula (I) in which Q is Q1, Y is S(O)_(m), R⁵ is hydrogen and n is 2

No. R¹ R³ R⁴ m X 1H NMR  1. Me Me Me 0 CH₂  2. Me Me Me 1 CH₂  3. Me Me Me 2 CH₂  4. Me Me Me 0 CHMe  5. Me Me Me 1 CHMe  6. Me Me Me 2 CHMe  7. Me Me Me 0 C(CH₃)₂ CDCl3, 400 MHz: 1.49 (s, 6H), 2.04 (dd, 2H), 2.28 (s, 3H), 2.62 (s, 3H), 2.98 (dd, 2H), 4.10 (s, 3H), 7.22 (s, 1H), 8.81 (s, 1H)  8. Me Me Me 1 C(CH₃)₂  9. Me Me Me 2 C(CH₃)₂ CDCl3, 400 MHz: 1.55 (s, 6H), 2.38 (dd, 2H), 2.64 (s, 3H), 2.81 (s, 3H), 3.43 (dd, 2H), 4.10 (s, 3H), 7.33 (s, 1H), 8.87 (s, 1H)  10. Me Me Me 0 C(OC₂H₄O)  11. Me Me Me 1 C(OC₂H₄O)  12. Me Me Me 2 C(OC₂H₄O)  13. Me Me Me 0 C(SC₂H₄S)  14. Me Me Me 1 C(SC₂H₄S)  15. Me Me Me 2 C(SC₂H₄S)  16. Me Me Me 0 CHOMe  17. Me Me Me 1 CHOMe  18. Me Me Me 2 CHOMe  19. Me Me Me 0 CHOEt  20. Me Me Me 1 CHOEt  21. Me Me Me 2 CHOEt  22. Me Me Me 0 CHOiPr  23. Me Me Me 1 CHOiPr  24. Me Me Me 2 CHOiPr  25. Me Me Me 0 CHOCH₂cPr  26. Me Me Me 1 CHOCH₂cPr  27. Me Me Me 2 CHOCH₂cPr  28. Me Me Me 0 CHOC₂H₄OMe  29. Me Me Me 1 CHOC₂H₄OMe  30. Me Me Me 2 CHOC₂H₄OMe  31. Me Me Me 0 CHOCH₂CCH  32. Me Me Me 1 CHOCH₂CCH  33. Me Me Me 2 CHOCH₂CCH  34. Me Me Me 0 CHOCH₂CH═CH₂  35. Me Me Me 1 CHOCH₂CH═CH₂  36. Me Me Me 2 CHOCH₂CH═CH₂  37. Me Me Me 0

 38. Me Me Me 1

 39. Me Me Me 2

 40. Me Me Me 0

CDCl3, 400 MHz: 8.28-8.25 (m, 2H), 8.19 (m, 1H), 7.62 (s, 1H), 6.52 (m, 1H), 4.13 (s, 3H), 3.81 (m, 1H), 3.30 (m, 1H), 2.92-2.74 (m, 2H), 2.80 (s, 3H), 2.32 (s, 3H)  41. Me Me Me 1

 42. Me Me Me 2

 43. Me Me Me 0

 44. Me Me Me 1

 45. Me Me Me 2

 46. Me Me Me 0

 47. Me Me Me 1

 48. Me Me Me 2

 49. Me Me Me 0

 50. Me Me Me 1

 51. Me Me Me 2

 52. Me Me Me 0 CHOC₂H₄F  53. Me Me Me 1 CHOC₂H₄F  54. Me Me Me 2 CHOC₂H₄F  55. Me Me Me 0 C═NOMe  56. Me Me Me 1 C═NOMe  57. Me Me Me 2 C═NOMe  58. Me Me Me 0 C═NOCH₂CCH  59. Me Me Me 1 C═NOCH₂CCH  60. Me Me Me 2 C═NOCH₂CCH  61. Me Me Me 0 C═NOCH₂CH═CH₂  62. Me Me Me 1 C═NOCH₂CH═CH₂  63. Me Me Me 2 C═NOCH₂CH═CH₂  64. Me Me Me 0 C═O  65. Me Me Me 1 C═O  66. Me Me Me 2 C═O  67. Me Me Me 0 C═S  68. Me Me Me 1 C═S  69. Me Me Me 2 C═S  70. Me Me Me 0 C═S  71. Me Me Me 1 C═S  72. Me Me Me 2 C═S  73. Me Me Me 0 C═N—N(CH₃)₂  74. Me Me Me 1 C═N—N(CH₃)₂  75. Me Me Me 2 C═N—N(CH₃)₂  76. Me Me Me 0 O  77. Me Me Me 1 O  78. Me Me Me 2 O  79. Me Me Me 0 S  80. Me Me Me 1 S  81. Me Me Me 2 S  82. Me Me Me 0 SO  83. Me Me Me 1 SO  84. Me Me Me 2 SO  85. Me Me Me 0 SO₂  86. Me Me Me 1 SO₂  87. Me Me Me 2 SO₂  88. Me Me Me 0 NMe  89. Me Me Me 1 NMe  90. Me Me Me 2 NMe  91. Me Me H 0 CH₂  92. Me Me H 1 CH₂  93. Me Me H 2 CH₂  94. Me Me H 0 CHMe  95. Me Me H 1 CHMe  96. Me Me H 2 CHMe  97. Me Me H 0 C(CH₃)₂  98. Me Me H 1 C(CH₃)₂  99. Me Me H 2 C(CH₃)₂ 100. Me Me H 0 C(OC₂H₄O) 101. Me Me H 1 C(OC₂H₄O) 102. Me Me H 2 C(OC₂H₄O) 103. Me Me H 0 C(SC₂H₄S) 104. Me Me H 1 C(SC₂H₄S) 105. Me Me H 2 C(SC₂H₄S) 106. Me Me H 0 CHOMe 107. Me Me H 1 CHOMe 108. Me Me H 2 CHOMe 109. Me Me H 0 CHOEt 110. Me Me H 1 CHOEt 111. Me Me H 2 CHOEt 112. Me Me H 0 CHOiPr 113. Me Me H 1 CHOiPr 114. Me Me H 2 CHOiPr 115. Me Me H 0 CHOCH₂cPr 116. Me Me H 1 CHOCH₂cPr 117. Me Me H 2 CHOCH₂cPr 118. Me Me H 0 CHOC₂H₄OMe 119. Me Me H 1 CHOC₂H₄OMe 120. Me Me H 2 CHOC₂H₄OMe 121. Me Me H 0 CHOCH₂CCH 122. Me Me H 1 CHOCH₂CCH 123. Me Me H 2 CHOCH₂CCH 124. Me Me H 0 CHOCH₂CH═CH₂ 125. Me Me H 1 CHOCH₂CH═CH₂ 126. Me Me H 2 CHOCH₂CH═CH₂ 127. Me Me H 0

128. Me Me H 1

129. Me Me H 2

130. Me Me H 0

131. Me Me H 1

132. Me Me H 2

133. Me Me H 0

134. Me Me H 1

135. Me Me H 2

136. Me Me H 0

137. Me Me H 1

138. Me Me H 2

139. Me Me H 0

140. Me Me H 1

141. Me Me H 2

142. Me Me H 0 CHOC₂H₄F 143. Me Me H 1 CHOC₂H₄F 144. Me Me H 2 CHOC₂H₄F 145. Me Me H 0 C═NOMe 146. Me Me H 1 C═NOMe 147. Me Me H 2 C═NOMe 148. Me Me H 0 C═NOCH₂CCH 149. Me Me H 1 C═NOCH₂CCH 150. Me Me H 2 C═NOCH₂CCH 151. Me Me H 0 C═NOCH₂CH═CH₂ 152. Me Me H 1 C═NOCH₂CH═CH₂ 153. Me Me H 2 C═NOCH₂CH═CH₂ 154. Me Me H 0 C═O 155. Me Me H 1 C═O 156. Me Me H 2 C═O 157. Me Me H 0 C═S 158. Me Me H 1 C═S 159. Me Me H 2 C═S 160. Me Me H 0 C═S 161. Me Me H 1 C═S 162. Me Me H 2 C═S 163. Me Me H 0 C═N—N(CH₃)₂ 164. Me Me H 1 C═N—N(CH₃)₂ 165. Me Me H 2 C═N—N(CH₃)₂ 166. Me Me H 0 O 167. Me Me H 1 O 168. Me Me H 2 O 169. Me Me H 0 S 170. Me Me H 1 S 171. Me Me H 2 S 172. Me Me H 0 SO 173. Me Me H 1 SO 174. Me Me H 2 SO 175. Me Me H 0 SO₂ 176. Me Me H 1 SO₂ 177. Me Me H 2 SO₂ 178. Me Me H 0 NMe 179. Me Me H 1 NMe 180. Me Me H 2 NMe 181. Et Me Me 0 CH₂ 182. Et Me Me 1 CH₂ 183. Et Me Me 2 CH₂ 184. Et Me Me 0 CHMe 185. Et Me Me 1 CHMe 186. Et Me Me 2 CHMe 187. Et Me Me 0 C(CH₃)₂ CDCl3, 400 MHz: 1.49 (s, 6H), 1.61 (t, 3H), 2.04 (dd, 2H), 2.29 (s, 3H), 2.62 (s, 3H), 2.99 (dd, 2H), 4.46 (q, 2H), 7.23 (s, 1H), 9.12 (s, 1H) 188. Et Me Me 1 C(CH₃)₂ 189. Et Me Me 2 C(CH₃)₂ CDCl3, 400 MHz: 1.56 (s, 6H), 1.64 (t, 3H), 2.36 (dd, 2H), 2.65 (s, 3H), 2.77 (s, 3H), 3.43 (dd, 2H), 4.46 (q, 2H), 7.37 (s, 1H), 10.16 (s, 1H) 190. Et Me Me 0 C(OC₂H₄O) 191. Et Me Me 1 C(OC₂H₄O) 192. Et Me Me 2 C(OC₂H₄O) 193. Et Me Me 0 C(SC₂H₄S) 194. Et Me Me 1 C(SC₂H₄S) 195. Et Me Me 2 C(SC₂H₄S) 196. Et Me Me 0 CHOMe 197. Et Me Me 1 CHOMe 198. Et Me Me 2 CHOMe 199. Et Me Me 0 CHOEt 200. Et Me Me 1 CHOEt 201. Et Me Me 2 CHOEt 202. Et Me Me 0 CHOiPr 203. Et Me Me 1 CHOiPr 204. Et Me Me 2 CHOiPr 205. Et Me Me 0 CHOCH₂cPr 206. Et Me Me 1 CHOCH₂cPr 207. Et Me Me 2 CHOCH₂cPr 208. Et Me Me 0 CHOC₂H₄OMe 209. Et Me Me 1 CHOC₂H₄OMe 210. Et Me Me 2 CHOC₂H₄OMe 211. Et Me Me 0 CHOCH₂CCH 212. Et Me Me 1 CHOCH₂CCH 213. Et Me Me 2 CHOCH₂CCH 214. Et Me Me 0 CHOCH₂CH═CH₂ 215. Et Me Me 1 CHOCH₂CH═CH₂ 216. Et Me Me 2 CHOCH₂CH═CH₂ 217. Et Me Me 0

218. Et Me Me 1

219. Et Me Me 1

220. Et Me Me 0

221. Et Me Me 1

222. Et Me Me 2

223. Et Me Me 0

224. Et Me Me 1

225. Et Me Me 2

226. Et Me Me 0

227. Et Me Me 1

228. Et Me Me 2

229. Et Me Me 0

230. Et Me Me 1

231. Et Me Me 2

232. Et Me Me 0 CHOC₂H₄F 233. Et Me Me 1 CHOC₂H₄F 234. Et Me Me 2 CHOC₂H₄F 235. Et Me Me 0 C═NOMe 236. Et Me Me 1 C═NOMe 237. Et Me Me 2 C═NOMe 238. Et Me Me 0 C═NOCH₂CCH 239. Et Me Me 1 C═NOCH₂CCH 240. Et Me Me 2 C═NOCH₂CCH 241. Et Me Me 0 C═NOCH₂CH═CH₂ 242. Et Me Me 1 C═NOCH₂CH═CH₂ 243. Et Me Me 2 C═NOCH₂CH═CH₂ 244. Et Me Me 0 C═O 245. Et Me Me 1 C═O 246. Et Me Me 2 C═O 247. Et Me Me 0 C═S 248. Et Me Me 1 C═S 249. Et Me Me 2 C═S 250. Et Me Me 0 C═S 251. Et Me Me 1 C═S 252. Et Me Me 2 C═S 253. Et Me Me 0 C═N—N(CH₃)₂ 254. Et Me Me 1 C═N—N(CH₃)₂ 255. Et Me Me 2 C═N—N(CH₃)₂ 256. Et Me Me 0 O 257. Et Me Me 1 O 258. Et Me Me 2 O 259. Et Me Me 0 S 260. Et Me Me 1 S 261. Et Me Me 2 S 262. Et Me Me 0 SO 263. Et Me Me 1 SO 264. Et Me Me 2 SO 265. Et Me Me 0 SO₂ 266. Et Me Me 1 SO₂ 267. Et Me Me 2 SO₂ 268. Et Me Me 0 NMe 269. Et Me Me 1 NMe 270. Et Me Me 2 NMe 271. Et Me H 0 CH₂ 272. Et Me H 1 CH₂ 273. Et Me H 2 CH₂ 274. Et Me H 0 CHMe 275. Et Me H 1 CHMe 276. Et Me H 2 CHMe 277. Et Me H 0 C(CH₃)₂ 278. Et Me H 1 C(CH₃)₂ 279. Et Me H 2 C(CH₃)₂ 280. Et Me H 0 C(OC₂H₄O) 281. Et Me H 1 C(OC₂H₄O) 282. Et Me H 2 C(OC₂H₄O) 283. Et Me H 0 C(SC₂H₄S) 284. Et Me H 1 C(SC₂H₄S) 285. Et Me H 2 C(SC₂H₄S) 286. Et Me H 0 CHOMe 287. Et Me H 1 CHOMe 288. Et Me H 2 CHOMe 289. Et Me H 0 CHOEt 290. Et Me H 1 CHOEt 291. Et Me H 2 CHOEt 292. Et Me H 0 CHOiPr 293. Et Me H 1 CHOiPr 294. Et Me H 2 CHOiPr 295. Et Me H 0 CHOCH₂cPr 296. Et Me H 1 CHOCH₂cPr 297. Et Me H 2 CHOCH₂cPr 298. Et Me H 0 CHOC₂H₄OMe 299. Et Me H 1 CHOC₂H₄OMe 300. Et Me H 2 CHOC₂H₄OMe 301. Et Me H 0 CHOCH₂CCH 302. Et Me H 1 CHOCH₂CCH 303. Et Me H 2 CHOCH₂CCH 304. Et Me H 0 CHOCH₂CH═CH₂ 305. Et Me H 1 CHOCH₂CH═CH₂ 306. Et Me H 2 CHOCH₂CH═CH₂ 307. Et Me H 0

308. Et Me H 1

309. Et Me H 2

310. Et Me H 0

311. Et Me H 1

312. Et Me H 2

313. Et Me H 0

314. Et Me H 1

315. Et Me H 2

316. Et Me H 0

317. Et Me H 1

318. Et Me H 2

319. Et Me H 0

320. Et Me H 1

321 Et Me H 2

322. Et Me H 0 CHOC₂H₄F 323. Et Me H 1 CHOC₂H₄F 324. Et Me H 2 CHOC₂H₄F 325. Et Me H 0 C═NOMe 326. Et Me H 1 C═NOMe 327. Et Me H 2 C═NOMe 328. Et Me H 0 C═NOCH₂CCH 329. Et Me H 1 C═NOCH₂CCH 330. Et Me H 2 C═NOCH₂CCH 331. Et Me H 0 C═NOCH₂CH═CH₂ 332. Et Me H 1 C═NOCH₂CH═CH₂ 333. Et Me H 2 C═NOCH₂CH═CH₂ 334. Et Me H 0 C═O 335. Et Me H 1 C═O 336. Et Me H 2 C═O 337. Et Me H 0 C═S 338. Et Me H 1 C═S 339. Et Me H 2 C═S 340. Et Me H 0 C═S 341. Et Me H 1 C═S 342. Et Me H 2 C═S 343. Et Me H 0 C═N—N(CH₃)₂ 344. Et Me H 1 C═N—N(CH₃)₂ 345. Et Me H 2 C═N—N(CH₃)₂ 346. Et Me H 0 O 347. Et Me H 1 O 348. Et Me H 2 O 349. Et Me H 0 S 350. Et Me H 1 S 351. Et Me H 2 S 352. Et Me H 0 SO 353. Et Me H 1 SO 354. Et Me H 2 SO 355. Et Me H 0 SO₂ 356. Et Me H 1 SO₂ 357. Et Me H 2 SO₂ 358. Et Me H 0 NMe 359. Et Me H 1 NMe 360. Et Me H 2 NMe

TABLE 2 Inventive compounds of the general formula (I) in which Q is Q2, Y is S(O)_(m), R⁵ is hydrogen and n is 2

Number R¹ R³ R⁴ m X 1H NMR 361. Me Me Me 0 CH₂ 362. Me Me Me 1 CH₂ 363. Me Me Me 2 CH₂ 364. Me Me Me 0 CHMe 365. Me Me Me 1 CHMe 366. Me Me Me 2 CHMe 367. Me Me Me 0 C(CH₃)₂ 368. Me Me Me 1 C(CH₃)₂ 369. Me Me Me 2 C(CH₃)₂ 370. Me Me Me 0 C(OC₂H₄O) 371. Me Me Me 1 C(OC₂H₄O) 372. Me Me Me 2 C(OC₂H₄O) 373. Me Me Me 0 C(SC₂H₄S) 374. Me Me Me 1 C(SC₂H₄S) 375. Me Me Me 2 C(SC₂H₄S) 376. Me Me Me 0 CHOMe 377. Me Me Me 1 CHOMe 378. Me Me Me 2 CHOMe 379. Me Me Me 0 CHOEt 380. Me Me Me 1 CHOEt 381. Me Me Me 2 CHOEt 382. Me Me Me 0 CHOiPr 383. Me Me Me 1 CHOiPr 384. Me Me Me 2 CHOiPr 385. Me Me Me 0 CHOCH₂cPr 386. Me Me Me 1 CHOCH₂cPr 387. Me Me Me 2 CHOCH₂cPr 388. Me Me Me 0 CHOC₂H₄OMe 389. Me Me Me 1 CHOC₂H₄OMe 390. Me Me Me 2 CHOC₂H₄OMe 391. Me Me Me 0 CHOCH₂CCH 392. Me Me Me 1 CHOCH₂CCH 393. Me Me Me 2 CHOCH₂CCH 394. Me Me Me 0 CHOCH₂CH═CH₂ 395. Me Me Me 1 CHOCH₂CH═CH₂ 396. Me Me Me 2 CHOCH₂CH═CH₂ 397. Me Me Me 0

398. Me Me Me 1

399. Me Me Me 2

400. Me Me Me 0

401. Me Me Me 1

402. Me Me Me 2

403. Me Me Me 0

404. Me Me Me 1

405. Me Me Me 2

406. Me Me Me 0

407. Me Me Me 1

408. Me Me Me 2

409. Me Me Me 0

410. Me Me Me 1

411. Me Me Me 2

412. Me Me Me 0 CHOC₂H₄F 413. Me Me Me 1 CHOC₂H₄F 414. Me Me Me 2 CHOC₂H₄F 415. Me Me Me 0 C═NOMe 416. Me Me Me 1 C═NOMe 417. Me Me Me 2 C═NOMe 418. Me Me Me 0 C═NOCH₂CCH 419. Me Me Me 1 C═NOCH₂CCH 420. Me Me Me 2 C═NOCH₂CCH 421. Me Me Me 0 C═NOCH₂CH═CH₂ 422. Me Me Me 1 C═NOCH₂CH═CH₂ 423. Me Me Me 2 C═NOCH₂CH═CH₂ 424. Me Me Me 0 C═O 425. Me Me Me 1 C═O 426. Me Me Me 2 C═O 427. Me Me Me 0 C═S 428. Me Me Me 1 C═S 429. Me Me Me 2 C═S 430. Me Me Me 0 C═S 431. Me Me Me 1 C═S 432. Me Me Me 2 C═S 433. Me Me Me 0 C═N—N(CH₃)₂ 434. Me Me Me 1 C═N—N(CH₃)₂ 435. Me Me Me 2 C═N—N(CH₃)₂ 436. Me Me Me 0 O 437. Me Me Me 1 O 438. Me Me Me 2 O 439. Me Me Me 0 S 440. Me Me Me 1 S 441. Me Me Me 2 S 442. Me Me Me 0 SO 443. Me Me Me 1 SO 444. Me Me Me 2 SO 445. Me Me Me 0 SO₂ 446. Me Me Me 1 SO₂ 447. Me Me Me 2 SO₂ 448. Me Me Me 0 NMe 449. Me Me Me 1 NMe 450. Me Me Me 2 NMe 451. Me Me H 0 CH₂ 452. Me Me H 1 CH₂ 453. Me Me H 2 CH₂ 454. Me Me H 0 CHMe 455. Me Me H 1 CHMe 456. Me Me H 2 CHMe 457. Me Me H 0 C(CH₃)₂ 458. Me Me H 1 C(CH₃)₂ 459. Me Me H 2 C(CH₃)₂ 460. Me Me H 0 C(OC₂H₄O) 461. Me Me H 1 C(OC₂H₄O) 462. Me Me H 2 C(OC₂H₄O) 463. Me Me H 0 C(SC₂H₄S) 464. Me Me H 1 C(SC₂H₄S) 465. Me Me H 2 C(SC₂H₄S) 466. Me Me H 0 CHOMe 467. Me Me H 1 CHOMe 468. Me Me H 2 CHOMe 469. Me Me H 0 CHOEt 470. Me Me H 1 CHOEt 471. Me Me H 2 CHOEt 472. Me Me H 0 CHOiPr 473. Me Me H 1 CHOiPr 474. Me Me H 2 CHOiPr 475. Me Me H 0 CHOCH₂cPr 476. Me Me H 1 CHOCH₂cPr 477. Me Me H 2 CHOCH₂cPr 478. Me Me H 0 CHOC₂H₄OMe 479. Me Me H 1 CHOC₂H₄OMe 480. Me Me H 2 CHOC₂H₄OMe 481. Me Me H 0 CHOCH₂CCH 482. Me Me H 1 CHOCH₂CCH 483. Me Me H 2 CHOCH₂CCH 484. Me Me H 0 CHOCH₂CH═CH₂ 485. Me Me H 1 CHOCH₂CH═CH₂ 486. Me Me H 2 CHOCH₂CH═CH₂ 487. Me Me H 0

488. Me Me H 1

489. Me Me H 2

490. Me Me H 0

491. Me Me H 1

492. Me Me H 2

493. Me Me H 0

494. Me Me H 1

495. Me Me H 2

496. Me Me H 0

497. Me Me H 1

498. Me Me H 2

499. Me Me H 0

500. Me Me H 1

501. Me Me H 2

502. Me Me H 0 CHOC₂H₄F 503. Me Me H 1 CHOC₂H₄F 504. Me Me H 2 CHOC₂H₄F 505. Me Me H 0 C═NOMe 506. Me Me H 1 C═NOMe 507. Me Me H 2 C═NOMe 508. Me Me H 0 C═NOCH₂CCH 509. Me Me H 1 C═NOCH₂CCH 510. Me Me H 2 C═NOCH₂CCH 511. Me Me H 0 C═NOCH₂CH═CH₂ 512. Me Me H 1 C═NOCH₂CH═CH₂ 513. Me Me H 2 C═NOCH₂CH═CH₂ 514. Me Me H 0 C═O 515. Me Me H 1 C═O 516. Me Me H 2 C═O 517. Me Me H 0 C═S 518. Me Me H 1 C═S 519. Me Me H 2 C═S 520. Me Me H 0 C═S 521. Me Me H 1 C═S 522. Me Me H 2 C═S 523. Me Me H 0 C═N—N(CH₃)₂ 524. Me Me H 1 C═N—N(CH₃)₂ 525. Me Me H 2 C═N—N(CH₃)₂ 526. Me Me H 0 O 527. Me Me H 1 O 528. Me Me H 2 O 529. Me Me H 0 S 530. Me Me H 1 S 531. Me Me H 2 S 532. Me Me H 0 SO 533. Me Me H 1 SO 534. Me Me H 2 SO 535. Me Me H 0 SO₂ 536. Me Me H 1 SO₂ 537. Me Me H 2 SO₂ 538. Me Me H 0 NMe 539. Me Me H 1 NMe 540. Me Me H 2 NMe 541. Et Me Me 0 CH₂ 542. Et Me Me 1 CH₂ 543. Et Me Me 2 CH₂ 544. Et Me Me 0 CHMe 545. Et Me Me 1 CHMe 546. Et Me Me 2 CHMe 547. Et Me Me 0 C(CH₃)₂ 548. Et Me Me 1 C(CH₃)₂ 549. Et Me Me 2 C(CH₃)₂ 550. Et Me Me 0 C(OC₂H₄O) 551. Et Me Me 1 C(OC₂H₄O) 552. Et Me Me 2 C(OC₂H₄O) 553. Et Me Me 0 C(SC₂H₄S) 554. Et Me Me 1 C(SC₂H₄S) 555. Et Me Me 2 C(SC₂H₄S) 556. Et Me Me 0 CHOMe 557. Et Me Me 1 CHOMe 558. Et Me Me 2 CHOMe 559. Et Me Me 0 CHOEt 560. Et Me Me 1 CHOEt 561. Et Me Me 2 CHOEt 562. Et Me Me 0 CHOiPr 563. Et Me Me 1 CHOiPr 564. Et Me Me 2 CHOiPr 565. Et Me Me 0 CHOCH₂cPr 566. Et Me Me 1 CHOCH₂cPr 567. Et Me Me 2 CHOCH₂cPr 568. Et Me Me 0 CHOC₂H₄OMe 569. Et Me Me 1 CHOC₂H₄OMe 570. Et Me Me 2 CHOC₂H₄OMe 571. Et Me Me 0 CHOCH₂CCH 572. Et Me Me 1 CHOCH₂CCH 573. Et Me Me 2 CHOCH₂CCH 574. Et Me Me 0 CHOCH₂CH═CH₂ 575. Et Me Me 1 CHOCH₂CH═CH₂ 576. Et Me Me 2 CHOCH₂CH═CH₂ 577. Et Me Me 0

578. Et Me Me 1

579. Et Me Me 2

580. Et Me Me 0

581. Et Me Me 1

582. Et Me Me 2

583. Et Me Me 0

584. Et Me Me 1

585. Et Me Me 2

586. Et Me Me 0

587. Et Me Me 1

588. Et Me Me 2

589. Et Me Me 0

590. Et Me Me 1

591. Et Me Me 2

592. Et Me Me 0 CHOC₂H₄F 593. Et Me Me 1 CHOC₂H₄F 594. Et Me Me 2 CHOC₂H₄F 595. Et Me Me 0 C═NOMe 596. Et Me Me 1 C═NOMe 597. Et Me Me 2 C═NOMe 598. Et Me Me 0 C═NOCH₂CCH 599. Et Me Me 1 C═NOCH₂CCH 600. Et Me Me 2 C═NOCH₂CCH 601. Et Me Me 0 C═NOCH₂CH═CH₂ 602. Et Me Me 1 C═NOCH₂CH═CH₂ 603. Et Me Me 2 C═NOCH₂CH═CH₂ 604. Et Me Me 0 C═O 605. Et Me Me 1 C═O 606. Et Me Me 2 C═O 607. Et Me Me 0 C═S 608. Et Me Me 1 C═S 609. Et Me Me 2 C═S 610. Et Me Me 0 C═S 611. Et Me Me 1 C═S 612. Et Me Me 2 C═S 613. Et Me Me 0 C═N—N(CH₃)₂ 614. Et Me Me 1 C═N—N(CH₃)₂ 615. Et Me Me 2 C═N—N(CH₃)₂ 616. Et Me Me 0 O 617. Et Me Me 1 O 618. Et Me Me 2 O 619. Et Me Me 0 S 620. Et Me Me 1 S 621. Et Me Me 2 S 622. Et Me Me 0 SO 623. Et Me Me 1 SO 624. Et Me Me 2 SO 625. Et Me Me 0 SO₂ 626. Et Me Me 1 SO₂ 627. Et Me Me 2 SO₂ 628. Et Me Me 0 NMe 629. Et Me Me 1 NMe 630. Et Me Me 2 NMe 631. Et Me H 0 CH₂ 632. Et Me H 1 CH₂ 633. Et Me H 2 CH₂ 634. Et Me H 0 CHMe 635. Et Me H 1 CHMe 636. Et Me H 2 CHMe 637. Et Me H 0 C(CH₃)₂ 638. Et Me H 1 C(CH₃)₂ 639. Et Me H 2 C(CH₃)₂ 640. Et Me H 0 C(OC₂H₄O) 641. Et Me H 1 C(OC₂H₄O) 642. Et Me H 2 C(OC₂H₄O) 643. Et Me H 0 C(SC₂H₄S) 644. Et Me H 1 C(SC₂H₄S) 645. Et Me H 2 C(SC₂H₄S) 646. Et Me H 0 CHOMe 647. Et Me H 1 CHOMe 648. Et Me H 2 CHOMe 649. Et Me H 0 CHOEt 650. Et Me H 1 CHOEt 651. Et Me H 2 CHOEt 652. Et Me H 0 CHOiPr 653. Et Me H 1 CHOiPr 654. Et Me H 2 CHOiPr 655. Et Me H 0 CHOCH₂cPr 656. Et Me H 1 CHOCH₂cPr 657. Et Me H 2 CHOCH₂cPr 658. Et Me H 0 CHOC₂H₄OMe 659. Et Me H 1 CHOC₂H₄OMe 660. Et Me H 2 CHOC₂H₄OMe 661. Et Me H 0 CHOCH₂CCH 662. Et Me H 1 CHOCH₂CCH 663. Et Me H 2 CHOCH₂CCH 664. Et Me H 0 CHOCH₂CH═CH₂ 665. Et Me H 1 CHOCH₂CH═CH₂ 666. Et Me H 2 CHOCH₂CH═CH₂ 667. Et Me H 0

668. Et Me H 1

669. Et Me H 2

670. Et Me H 0

671. Et Me H 1

672. Et Me H 2

673. Et Me H 0

674. Et Me H 1

675. Et Me H 2

676. Et Me H 0

677. Et Me H 1

678. Et Me H 2

679. Et Me H 0

680. Et Me H 1

681. Et Me H 2

682. Et Me H 0 CHOC₂H₄F 683. Et Me H 1 CHOC₂H₄F 684. Et Me H 2 CHOC₂H₄F 685. Et Me H 0 C═NOMe 686. Et Me H 1 C═NOMe 687. Et Me H 2 C═NOMe 688. Et Me H 0 C═NOCH₂CCH 689. Et Me H 1 C═NOCH₂CCH 690. Et Me H 2 C═NOCH₂CCH 691. Et Me H 0 C═NOCH₂CH═CH₂ 692. Et Me H 1 C═NOCH₂CH═CH₂ 693. Et Me H 2 C═NOCH₂CH═CH₂ 694. Et Me H 0 C═O 695. Et Me H 1 C═O 696. Et Me H 2 C═O 697. Et Me H 0 C═S 698. Et Me H 1 C═S 699. Et Me H 2 C═S 700. Et Me H 0 C═S 701. Et Me H 1 C═S 702. Et Me H 2 C═S 703. Et Me H 0 C═N—N(CH₃)₂ 704. Et Me H 1 C═N—N(CH₃)₂ 705. Et Me H 2 C═N—N(CH₃)₂ 706. Et Me H 0 O 707. Et Me H 1 O 708. Et Me H 2 O 709. Et Me H 0 S 710. Et Me H 1 S 711. Et Me H 2 S 712. Et Me H 0 SO 713. Et Me H 1 SO 714. Et Me H 2 SO 715. Et Me H 0 SO₂ 716. Et Me H 1 SO₂ 717. Et Me H 2 SO₂ 718. Et Me H 0 NMe 719. Et Me H 1 NMe 720. Et Me H 2 NMe

TABLE 3 Inventive compounds of the general formula (I) in which Q is Q3, Y is S(O)_(m), R⁵ is hydrogen and n is 2

No. R² R³ R⁴ m X 1H NMR  721. Me Me Me 0 CH₂  722. Me Me Me 1 CH₂  723. Me Me Me 2 CH₂  724. Me Me Me 0 CHMe  725. Me Me Me 1 CHMe  726. Me Me Me 2 CHMe  727. Me Me Me 0 C(CH₃)₂  728. Me Me Me 1 C(CH₃)₂  729. Me Me Me 2 C(CH₃)₂  730. Me Me Me 0 C(OC₂H₄O)  731. Me Me Me 1 C(OC₂H₄O)  732. Me Me Me 2 C(OC₂H₄O)  733. Me Me Me 0 C(SC₂H₄S)  734. Me Me Me 1 C(SC₂H₄S)  735. Me Me Me 2 C(SC₂H₄S)  736. Me Me Me 0 CHOMe  737. Me Me Me 1 CHOMe  738. Me Me Me 2 CHOMe  739. Me Me Me 0 CHOEt  740. Me Me Me 1 CHOEt  741. Me Me Me 2 CHOEt  742. Me Me Me 0 CHOiPr  743. Me Me Me 1 CHOiPr  744. Me Me Me 2 CHOiPr  745. Me Me Me 0 CHOCH₂cPr  746. Me Me Me 1 CHOCH₂cPr  747. Me Me Me 2 CHOCH₂cPr  748. Me Me Me 0 CHOC₂H₄OMe  749. Me Me Me 1 CHOC₂H₄OMe  750. Me Me Me 2 CHOC₂H₄OMe  751. Me Me Me 0 CHOCH₂CCH  752. Me Me Me 1 CHOCH₂CCH  753. Me Me Me 2 CHOCH₂CCH  754. Me Me Me 0 CHOCH₂CH═CH₂  755. Me Me Me 1 CHOCH₂CH═CH₂  756. Me Me Me 2 CHOCH₂CH═CH₂  757. Me Me Me 0

 758. Me Me Me 1

 759. Me Me Me 2

 760. Me Me Me 0

 761. Me Me Me 1

 762. Me Me Me 2

DMSO-d₆, 400 MHz: 11.42 (s, 1H), 8.39 (s, 1H), 8.35-8.30 (m, 2H), 7.70 (s, 1H), 6.52 (dd, 1H), 3.79- 3.69 (m, 1H), 3.61- 3.52 (m, 1H), 2.80- 2.60 (m, 5H), 2.38 (s, 3H), 2.21 (s, 3H)  763. Me Me Me 0

 764. Me Me Me 1

 765. Me Me Me 2

 766. Me Me Me 0

 767. Me Me Me 1

 768. Me Me Me 2

 769. Me Me Me 0

 770. Me Me Me 1

 771. Me Me Me 2

 772. Me Me Me 0 CHOC₂H₄F  773. Me Me Me 1 CHOC₂H₄F  774. Me Me Me 2 CHOC₂H₄F  775. Me Me Me 0 C═NOMe  776. Me Me Me 1 C═NOMe  777. Me Me Me 2 C═NOMe  778. Me Me Me 0 C═NOCH₂CCH  779. Me Me Me 1 C═NOCH₂CCH  780. Me Me Me 2 C═NOCH₂CCH  781. Me Me Me 0 C═NOCH₂CH═CH₂  782. Me Me Me 1 C═NOCH₂CH═CH₂  783. Me Me Me 2 C═NOCH₂CH═CH₂  784. Me Me Me 0 C═O  785. Me Me Me 1 C═O  786. Me Me Me 2 C═O  787. Me Me Me 0 C═S  788. Me Me Me 1 C═S  789. Me Me Me 2 C═S  790. Me Me Me 0 C═S  791. Me Me Me 1 C═S  792. Me Me Me 2 C═S  793. Me Me Me 0 C═N—N(CH₃)₂  794. Me Me Me 1 C═N—N(CH₃)₂  795. Me Me Me 2 C═N—N(CH₃)₂  796. Me Me Me 0 O  797. Me Me Me 1 O  798. Me Me Me 2 O  799. Me Me Me 0 S  800. Me Me Me 1 S  801. Me Me Me 2 S  802. Me Me Me 0 SO  803. Me Me Me 1 SO  804. Me Me Me 2 SO  805. Me Me Me 0 SO₂  806. Me Me Me 1 SO₂  807. Me Me Me 2 SO₂  808. Me Me Me 0 NMe  809. Me Me Me 1 NMe  810. Me Me Me 2 NMe  811. Me Me H 0 CH₂  812. Me Me H 1 CH₂  813. Me Me H 2 CH₂  814. Me Me H 0 CHMe  815. Me Me H 1 CHMe  816. Me Me H 2 CHMe  817. Me Me H 0 C(CH₃)₂  818. Me Me H 1 C(CH₃)₂  819. Me Me H 2 C(CH₃)₂  820. Me Me H 0 C(OC₂H₄O)  821. Me Me H 1 C(OC₂H₄O)  822. Me Me H 2 C(OC₂H₄O)  823. Me Me H 0 C(SC₂H₄S)  824. Me Me H 1 C(SC₂H₄S)  825. Me Me H 2 C(SC₂H₄S)  826. Me Me H 0 CHOMe  827. Me Me H 1 CHOMe  828. Me Me H 2 CHOMe  829. Me Me H 0 CHOEt  830. Me Me H 1 CHOEt  831. Me Me H 2 CHOEt  832. Me Me H 0 CHOiPr  833. Me Me H 1 CHOiPr  834. Me Me H 2 CHOiPr  835. Me Me H 0 CHOCH₂cPr  836. Me Me H 1 CHOCH₂cPr  837. Me Me H 2 CHOCH₂cPr  838. Me Me H 0 CHOC₂H₄OMe  839. Me Me H 1 CHOC₂H₄OMe  840. Me Me H 2 CHOC₂H₄OMe  841. Me Me H 0 CHOCH₂CCH  842. Me Me H 1 CHOCH₂CCH  843. Me Me H 2 CHOCH₂CCH  844. Me Me H 0 CHOCH₂CH═CH₂  845. Me Me H 1 CHOCH₂CH═CH₂  846. Me Me H 2 CHOCH₂CH═CH₂  847. Me Me H 0

 848. Me Me H 1

 849. Me Me H 2

 850. Me Me H 0

 851. Me Me H 1

 852. Me Me H 2

 853. Me Me H 0

 854. Me Me H 1

 855. Me Me H 2

 856. Me Me H 0

 857. Me Me H 1

 858. Me Me H 2

 859. Me Me H 0

 860. Me Me H 1

 861. Me Me H 2

 862. Me Me H 0 CHOC₂H₄F  863. Me Me H 1 CHOC₂H₄F  864. Me Me H 2 CHOC₂H₄F  865. Me Me H 0 C═NOMe  866. Me Me H 1 C═NOMe  867. Me Me H 2 C═NOMe  868. Me Me H 0 C═NOCH₂CCH  869. Me Me H 1 C═NOCH₂CCH  870. Me Me H 2 C═NOCH₂CCH  871. Me Me H 0 C═NOCH₂CH═CH₂  872. Me Me H 1 C═NOCH₂CH═CH₂  873. Me Me H 2 C═NOCH₂CH═CH₂  874. Me Me H 0 C═O  875. Me Me H 1 C═O  876. Me Me H 2 C═O  877. Me Me H 0 C═S  878. Me Me H 1 C═S  879. Me Me H 2 C═S  880. Me Me H 0 C═S  881. Me Me H 1 C═S  882. Me Me H 2 C═S  883. Me Me H 0 C═N—N(CH₃)₂  884. Me Me H 1 C═N—N(CH₃)₂  885. Me Me H 2 C═N—N(CH₃)₂  886. Me Me H 0 O  887. Me Me H 1 O  888. Me Me H 2 O  889. Me Me H 0 S  890. Me Me H 1 S  891. Me Me H 2 S  892. Me Me H 0 SO  893. Me Me H 1 SO  894. Me Me H 2 SO  895. Me Me H 0 SO₂  896. Me Me H 1 SO₂  897. Me Me H 2 SO₂  898. Me Me H 0 NMe  899. Me Me H 1 NMe  900. Me Me H 2 NMe  901. Et Me Me 0 CH₂  902. Et Me Me 1 CH₂  903. Et Me Me 2 CH₂  904. Et Me Me 0 CHMe  905. Et Me Me 1 CHMe  906. Et Me Me 2 CHMe  907. Et Me Me 0 C(CH₃)₂  908. Et Me Me 1 C(CH₃)₂  909. Et Me Me 2 C(CH₃)₂  910. Et Me Me 0 C(OC₂H₄O)  911. Et Me Me 1 C(OC₂H₄O)  912. Et Me Me 2 C(OC₂H₄O)  913. Et Me Me 0 C(SC₂H₄S)  914. Et Me Me 1 C(SC₂H₄S)  915. Et Me Me 2 C(SC₂H₄S)  916. Et Me Me 0 CHOMe  917. Et Me Me 1 CHOMe  918. Et Me Me 2 CHOMe  919. Et Me Me 0 CHOEt  920. Et Me Me 1 CHOEt  921. Et Me Me 2 CHOEt  922. Et Me Me 0 CHOiPr  923. Et Me Me 1 CHOiPr  924. Et Me Me 2 CHOiPr  925. Et Me Me 0 CHOCH₂cPr  926. Et Me Me 1 CHOCH₂cPr  927. Et Me Me 2 CHOCH₂cPr  928. Et Me Me 0 CHOC₂H₄OMe  929. Et Me Me 1 CHOC₂H₄OMe  930. Et Me Me 2 CHOC₂H₄OMe  931. Et Me Me 0 CHOCH₂CCH  932. Et Me Me 1 CHOCH₂CCH  933. Et Me Me 2 CHOCH₂CCH  934. Et Me Me 0 CHOCH₂CH═CH₂  935. Et Me Me 1 CHOCH₂CH═CH₂  936. Et Me Me 2 CHOCH₂CH═CH₂  937. Et Me Me 0

 938. Et Me Me 1

 939. Et Me Me 2

 940. Et Me Me 0

 941. Et Me Me 1

 942. Et Me Me 2

DMSO-d₆, 400 MHz: 11.35 (s, 1H), 8.39 (s, 1H), 8.34-8.30 (m, 2H), 7.67 (s, 1H), 6.52 (dd, 1H), 3.80- 3.71 (m, 1H), 3.60- 3.53 (m, 1H), 2.82- 2.60 (m, 7H), 2.20 (s, 3H), 1.26 (t, 3H)  943. Et Me Me 0

 944. Et Me Me 1

 945. Et Me Me 2

 946. Et Me Me 0

 947. Et Me Me 1

 948. Et Me Me 2

 949. Et Me Me 0

 950. Et Me Me 1

 951. Et Me Me 2

 952. Et Me Me 0 CHOC₂H₄F  953. Et Me Me 1 CHOC₂H₄F  954. Et Me Me 2 CHOC₂H₄F  955. Et Me Me 0 C═NOMe  956. Et Me Me 1 C═NOMe  957. Et Me Me 2 C═NOMe  958. Et Me Me 0 C═NOCH₂CCH  959. Et Me Me 1 C═NOCH₂CCH  960. Et Me Me 2 C═NOCH₂CCH  961. Et Me Me 0 C═NOCH₂CH═CH₂  962. Et Me Me 1 C═NOCH₂CH═CH₂  963. Et Me Me 2 C═NOCH₂CH═CH₂  964. Et Me Me 0 C═O  965. Et Me Me 1 C═O  966. Et Me Me 2 C═O  967. Et Me Me 0 C═S  968. Et Me Me 1 C═S  969. Et Me Me 2 C═S  970. Et Me Me 0 C═S  971. Et Me Me 1 C═S  972. Et Me Me 2 C═S  973. Et Me Me 0 C═N—N(CH₃)₂  974. Et Me Me 1 C═N—N(CH₃)₂  975. Et Me Me 2 C═N—N(CH₃)₂  976. Et Me Me 0 O  977. Et Me Me 1 O  978. Et Me Me 2 O  979. Et Me Me 0 S  980. Et Me Me 1 S  981. Et Me Me 2 S  982. Et Me Me 0 SO  983. Et Me Me 1 SO  984. Et Me Me 2 SO  985. Et Me Me 0 SO₂  986. Et Me Me 1 SO₂  987. Et Me Me 2 SO₂  988. Et Me Me 0 NMe  989. Et Me Me 1 NMe  990. Et Me Me 2 NMe  991. Et Me H 0 CH₂  992. Et Me H 1 CH₂  993. Et Me H 2 CH₂  994. Et Me H 0 CHMe  995. Et Me H 1 CHMe  996. Et Me H 2 CHMe  997. Et Me H 0 C(CH₃)₂  998. Et Me H 1 C(CH₃)₂  999. Et Me H 2 C(CH₃)₂ 1000 Et Me H 0 C(OC₂H₄O) 1001 Et Me H 1 C(OC₂H₄O) 1002 Et Me H 2 C(OC₂H₄O) 1003 Et Me H 0 C(SC₂H₄S) 1004 Et Me H 1 C(SC₂H₄S) 1005 Et Me H 2 C(SC₂H₄S) 1006 Et Me H 0 CHOMe 1007 Et Me H 1 CHOMe 1008 Et Me H 2 CHOMe 1009 Et Me H 0 CHOEt 1010 Et Me H 1 CHOEt 1011 Et Me H 2 CHOEt 1012 Et Me H 0 CHOiPr 1013 Et Me H 1 CHOiPr 1014 Et Me H 2 CHOiPr 1015 Et Me H 0 CHOCH₂cPr 1016 Et Me H 1 CHOCH₂cPr 1017 Et Me H 2 CHOCH₂cPr 1018 Et Me H 0 CHOC₂H₄OMe 1019 Et Me H 1 CHOC₂H₄OMe 1020 Et Me H 2 CHOC₂H₄OMe 1021 Et Me H 0 CHOCH₂CCH 1022 Et Me H 1 CHOCH₂CCH 1023 Et Me H 2 CHOCH₂CCH 1024 Et Me H 0 CHOCH₂CH═CH₂ 1025 Et Me H 1 CHOCH₂CH═CH₂ 1026 Et Me H 2 CHOCH₂CH═CH₂ 1027 Et Me H 0

1028 Et Me H 1

1029 Et Me H 2

1030 Et Me H 0

1031 Et Me H 1

1032 Et Me H 2

1033 Et Me H 0

1034 Et Me H 1

1035 Et Me H 2

1036 Et Me H 0

1037 Et Me H 1

1038 Et Me H 2

1039 Et Me H 0

1040 Et Me H 1

1041 Et Me H 2

1042 Et Me H 0 CHOC₂H₄F 1043 Et Me H 1 CHOC₂H₄F 1044 Et Me H 2 CHOC₂H₄F 1045 Et Me H 0 C═NOMe 1046 Et Me H 1 C═NOMe 1047 Et Me H 2 C═NOMe 1048 Et Me H 0 C═NOCH₂CCH 1049 Et Me H 1 C═NOCH₂CCH 1050 Et Me H 2 C═NOCH₂CCH 1051 Et Me H 0 C═NOCH₂CH═CH₂ 1052 Et Me H 1 C═NOCH₂CH═CH₂ 1053 Et Me H 2 C═NOCH₂CH═CH₂ 1054 Et Me H 0 C═O 1055 Et Me H 1 C═O 1056 Et Me H 2 C═O 1057 Et Me H 0 C═S 1058 Et Me H 1 C═S 1059 Et Me H 2 C═S 1060 Et Me H 0 C═S 1061 Et Me H 1 C═S 1062 Et Me H 2 C═S 1063 Et Me H 0 C═N—N(CH₃)₂ 1064 Et Me H 1 C═N—N(CH₃)₂ 1065 Et Me H 2 C═N—N(CH₃)₂ 1066 Et Me H 0 O 1067 Et Me H 1 O 1068 Et Me H 2 O 1069 Et Me H 0 S 1070 Et Me H 1 S 1071 Et Me H 2 S 1072 Et Me H 0 SO 1073 Et Me H 1 SO 1074 Et Me H 2 SO 1075 Et Me H 0 SO₂ 1076 Et Me H 1 SO₂ 1077 Et Me H 2 SO₂ 1078 Et Me H 0 NMe 1079 Et Me H 1 NMe 1080 Et Me H 2 NMe

TABLE 4 Inventive compounds of the general formula (I) in which Q is Q1, R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ Y X 1H NMR 1081. Me Me Me S CH₂ 1082. Me Me Me SO CH₂ 1083. Me Me Me SO₂ CH₂ 1084. Me Me Me S CHMe 1085. Me Me Me SO CHMe 1086. Me Me Me SO₂ CHMe 1087. Me Me Me S C(CH₃)₂ 1088. Me Me Me SO C(CH₃)₂ 1089. Me Me Me SO₂ C(CH₃)₂ 1090. Me Me Me S C(OC₂H₄O) 1091. Me Me Me SO C(OC₂H₄O) 1092. Me Me Me SO₂ C(OC₂H₄O) 1093. Me Me Me S C(SC₂H₄S) 1094. Me Me Me SO C(SC₂H₄S) 1095. Me Me Me SO₂ C(SC₂H₄S) 1096. Me Me Me S CHOMe 1097. Me Me Me SO CHOMe 1098. Me Me Me SO₂ CHOMe 1099. Me Me Me S CHOEt 1100. Me Me Me SO CHOEt 1101. Me Me Me SO₂ CHOEt 1102. Me Me Me S CHOiPr 1103. Me Me Me SO CHOiPr 1104. Me Me Me SO₂ CHOiPr 1105. Me Me Me S CHOCH₂cPr 1106. Me Me Me SO CHOCH₂cPr 1107. Me Me Me SO₂ CHOCH₂cPr 1108. Me Me Me S CHOC₂H₄OMe 1109. Me Me Me SO CHOC₂H₄OMe 1110. Me Me Me SO₂ CHOC₂H₄OMe 1111. Me Me Me S CHOCH₂CCH 1112. Me Me Me SO CHOCH₂CCH 1113. Me Me Me SO₂ CHOCH₂CCH 1114. Me Me Me S CHOCH₂CH═CH₂ 1115. Me Me Me SO CHOCH₂CH═CH₂ 1116. Me Me Me SO₂ CHOCH₂CH═CH₂ 1117. Me Me Me S

1118. Me Me Me SO

1119. Me Me Me SO₂

1120. Me Me Me S

1121. Me Me Me SO

1122. Me Me Me SO₂

1123. Me Me Me S

1124. Me Me Me SO

1125. Me Me Me SO₂

1126. Me Me Me S

1127. Me Me Me SO

1128. Me Me Me SO₂

1129. Me Me Me S

1130. Me Me Me SO

1131. Me Me Me SO₂

1132. Me Me Me S CHOC₂H₄F 1133. Me Me Me SO CHOC₂H₄F 1134. Me Me Me SO₂ CHOC₂H₄F 1135. Me Me Me S C═NOMe 1136. Me Me Me SO C═NOMe 1137. Me Me Me SO₂ C═NOMe 1138. Me Me Me S C═NOCH₂CCH 1139. Me Me Me SO C═NOCH₂CCH 1140. Me Me Me SO₂ C═NOCH₂CCH 1141. Me Me Me S C═NOCH₂CH═CH₂ 1142. Me Me Me SO C═NOCH₂CH═CH₂ 1143. Me Me Me SO₂ C═NOCH₂CH═CH₂ 1144. Me Me Me S C═O 1145. Me Me Me SO C═O 1146. Me Me Me SO₂ C═O 1147. Me Me Me S C═S 1148. Me Me Me SO C═S 1149. Me Me Me SO₂ C═S 1150. Me Me Me S C═S 1151. Me Me Me SO C═S 1152. Me Me Me SO₂ C═S 1153. Me Me Me S C═N—N(CH₃)₂ 1154. Me Me Me SO C═N—N(CH₃)₂ 1155. Me Me Me SO₂ C═N—N(CH₃)₂ 1156. Me Me Me S O 1157. Me Me Me SO O 1158. Me Me Me SO₂ O 1159. Me Me Me S S 1160. Me Me Me SO S 1161. Me Me Me SO₂ S 1162. Me Me Me S SO 1163. Me Me Me SO SO 1164. Me Me Me SO₂ SO 1165. Me Me Me S SO₂ 1166. Me Me Me SO SO₂ 1167. Me Me Me SO₂ SO₂ 1168. Me Me Me S NMe 1169. Me Me Me SO NMe 1170. Me Me Me SO₂ NMe 1171. Me Me Me O O 1172. Me Me H O O DMSO-d6, 400 MHz: 11.33 (s, 1H), 7.34 (d, 1H), 6.92 (d, 1H), 6.12 (s, 2H), 3.93 (s, 3H), 2.30 (s, 3H) 1173. Me SMe H O O DMSO-d6, 400 MHz: 11.50 (bs, 1H), 7.21 (d, 1H), 6.99 (d, 1H), 6.18 (s, 2H), 3.96 (s, 3H), 2.44 (s, 3H) 1174. Me Cl H O O 1175. Me Cl H S CH₂ 1176. Me Cl H SO CH₂ 1177. Me Cl H SO₂ CH₂ DMSO, 400 MHz: 3.41 (t, 2H), 3.76 (t, 2H), 4.02 (s, 3H), 7.94 (s, 2H), 11.95 (s, 1H) 1178. Me Cl H S CHMe 1179. Me Cl H SO CHMe 1180. Me Cl H SO₂ CHMe 1181. Me Cl H S C(CH₃)₂ 1182. Me Cl H SO C(CH₃)₂ 1183. Me Cl H SO₂ C(CH₃)₂ 1184. Me Cl H S C(OC₂H₄O) 1185. Me Cl H SO C(OC₂H₄O) 1186. Me Cl H SO₂ C(OC₂H₄O) 1187. Me Cl H S C(SC₂H₄S) 1188. Me Cl H SO C(SC₂H₄S) 1189. Me Cl H SO₂ C(SC₂H₄S) 1190. Me Cl H S CHOMe 1191. Me Cl H SO CHOMe 1192. Me Cl H SO₂ CHOMe CDCl3, 400 MHz: 3.57 (s, 3H), 3.68 (dd, 1H), 3.81 (d, 1H), 4.13 (s, 3H), 5.25 (d, 1H), 7.80 (d, 1H), 7.98 (d, 1H), 9.85 (s, 1H) 1193. Me Cl H S CHOEt 1194. Me Cl H SO CHOEt 1195. Me Cl H SO₂ CHOEt 1196. Me Cl H S CHOiPr 1197. Me Cl H SO CHOiPr 1198. Me Cl H SO₂ CHOiPr 1199. Me Cl H S CHOCH₂cPr 1200. Me Cl H SO CHOCH₂cPr 1201. Me Cl H SO₂ CHOCH₂cPr 1202. Me Cl H S CHOC₂H₄OMe 1203. Me Cl H SO CHOC₂H₄OMe 1204. Me Cl H SO₂ CHOC₂H₄OMe 1205. Me Cl H S CHOCH₂CCH 1206. Me Cl H SO CHOCH₂CCH 1207. Me Cl H SO₂ CHOCH₂CCH 1208. Me Cl H S CHOCH₂CH═CH₂ 1209. Me Cl H SO CHOCH₂CH═CH₂ 1210. Me Cl H SO₂ CHOCH₂CH═CH₂ 1211. Me Cl H S

1212. Me Cl H SO

1213. Me Cl H SO₂

1214. Me Cl H S

1215. Me Cl H SO

1216. Me Cl H SO₂

1217. Me Cl H S

1218. Me Cl H SO

1219. Me Cl H SO₂

1220. Me Cl H S

1221. Me Cl H SO

1222. Me Cl H SO₂

1223. Me Cl H S

1224. Me Cl H SO

1225. Me Cl H SO₂

1226. Me Cl H S CHOC₂H₄F 1227. Me Cl H SO CHOC₂H₄F 1228. Me Cl H SO₂ CHOC₂H₄F 1229. Me Cl H S C═NOMe 1230. Me Cl H SO C═NOMe 1231. Me Cl H SO₂ C═NOMe 1232. Me Cl H S C═NOCH₂CCH 1233. Me Cl H SO C═NOCH₂CCH 1234. Me Cl H SO₂ C═NOCH₂CCH 1235. Me Cl H S C═NOCH₂CH═CH₂ 1236. Me Cl H SO C═NOCH₂CH═CH₂ 1237. Me Cl H SO₂ C═NOCH₂CH═CH₂ 1238. Me Cl H S C═O 1239. Me Cl H SO C═O 1240. Me Cl H SO₂ C═O 1241. Me Cl H S C═S 1242. Me Cl H SO C═S 1243. Me Cl H SO₂ C═S 1244. Me Cl H S C═S 1245. Me Cl H SO C═S 1246. Me Cl H SO₂ C═S 1247. Me Cl H S C═N—N(CH₃)₂ 1248. Me Cl H SO C═N—N(CH₃)₂ 1249. Me Cl H SO₂ C═N—N(CH₃)₂ 1250. Me Cl H S O 1251. Me Cl H SO O 1252. Me Cl H SO₂ O 1253. Me Cl H S S 1254. Me Cl H SO S 1255. Me Cl H SO₂ S 1256. Me Cl H S SO 1257. Me Cl H SO SO 1258. Me Cl H SO₂ SO 1259. Me Cl H S SO₂ 1260. Me Cl H SO SO₂ 1261. Me Cl H SO₂ SO₂ 1262. Me Cl H S NMe 1263. Me Cl H SO NMe 1264. Me Cl H SO₂ NMe 1265. Et Me Me S CH₂ 1266. Et Me Me SO CH₂ 1267. Et Me Me SO₂ CH₂ 1268. Et Me Me S CHMe 1269. Et Me Me SO CHMe 1270. Et Me Me SO₂ CHMe 1271. Et Me Me S C(CH₃)₂ 1272. Et Me Me SO C(CH₃)₂ 1273. Et Me Me SO₂ C(CH₃)₂ 1274. Et Me Me S C(OC₂H₄O) 1275. Et Me Me SO C(OC₂H₄O) 1276. Et Me Me SO₂ C(OC₂H₄O) 1277. Et Me Me S C(SC₂H₄S) 1278. Et Me Me SO C(SC₂H₄S) 1279. Et Me Me SO₂ C(SC₂H₄S) 1280. Et Me Me S CHOMe 1281. Et Me Me SO CHOMe 1282. Et Me Me SO₂ CHOMe 1283. Et Me Me S CHOEt 1284. Et Me Me SO CHOEt 1285. Et Me Me SO₂ CHOEt 1286. Et Me Me S CHOiPr 1287. Et Me Me SO CHOiPr 1288. Et Me Me SO₂ CHOiPr 1289. Et Me Me S CHOCH₂cPr 1290. Et Me Me SO CHOCH₂cPr 1291. Et Me Me SO₂ CHOCH₂cPr 1292. Et Me Me S CHOC₂H₄OMe 1293. Et Me Me SO CHOC₂H₄OMe 1294. Et Me Me SO₂ CHOC₂H₄OMe 1295. Et Me Me S CHOCH₂CCH 1296. Et Me Me SO CHOCH₂CCH 1297. Et Me Me SO₂ CHOCH₂CCH 1298. Et Me Me S CHOCH₂CH═CH₂ 1299. Et Me Me SO CHOCH₂CH═CH₂ 1300. Et Me Me SO₂ CHOCH₂CH═CH₂ 1301. Et Me Me S

1302. Et Me Me SO

1303. Et Me Me SO₂

1304. Et Me Me S

1305. Et Me Me SO

1306. Et Me Me SO₂

1307. Et Me Me S

1308. Et Me Me SO

1309. Et Me Me SO₂

1310. Et Me Me S

1311. Et Me Me SO

1312. Et Me Me SO₂

1313. Et Me Me S

1314. Et Me Me SO

1315. Et Me Me SO₂

1316. Et Me Me S CHOC₂H₄F 1317. Et Me Me SO CHOC₂H₄F 1318. Et Me Me SO₂ CHOC₂H₄F 1319. Et Me Me S C═NOMe 1320. Et Me Me SO C═NOMe 1321. Et Me Me SO₂ C═NOMe 1322. Et Me Me S C═NOCH₂CCH 1323. Et Me Me SO C═NOCH₂CCH 1324. Et Me Me SO₂ C═NOCH₂CCH 1325. Et Me Me S C═NOCH₂CH═CH₂ 1326. Et Me Me SO C═NOCH₂CH═CH₂ 1327. Et Me Me SO₂ C═NOCH₂CH═CH₂ 1328. Et Me Me S C═O 1329. Et Me Me SO C═O 1330. Et Me Me SO₂ C═O 1331. Et Me Me S C═S 1332. Et Me Me SO C═S 1333. Et Me Me SO₂ C═S 1334. Et Me Me S C═S 1335. Et Me Me SO C═S 1336. Et Me Me SO₂ C═S 1337. Et Me Me S C═N—N(CH₃)₂ 1338. Et Me Me SO C═N—N(CH₃)₂ 1339. Et Me Me SO₂ C═N—N(CH₃)₂ 1340. Et Me Me S O 1341. Et Me Me SO O 1342. Et Me Me SO₂ O 1343. Et Me Me S S 1344. Et Me Me SO S 1345. Et Me Me SO₂ S 1346. Et Me Me S SO 1347. Et Me Me SO SO 1348. Et Me Me SO₂ SO 1349. Et Me Me S SO₂ 1350. Et Me Me SO SO₂ 1351. Et Me Me SO₂ SO₂ 1352. Et Me Me S NMe 1353. Et Me Me SO NMe 1354. Et Me Me SO₂ NMe 1355. Et Me Me O O 1356. Et Me H O O CDCl3, 400 MHz: 9.65 (s, 1H), 7.42 (d, 1H), 6.79 (d, 1H), 6.06 (s, 2H), 4.43 (q, 2H), 2.41 (s, 3H), 1.60 (t, 3H) 1357. Et SMe H O O 1358. Et Cl H O O 1359. Et Cl H S CH₂ 1360. Et Cl H SO CH₂ 1361. Et Cl H SO₂ CH₂ DMSO, 400 MHz: 1.48 (t, 3H), 3.42 (t, 2H), 3.75 (t, 2H), 4.38 (q, 2H), 7.93 (s, 2H), 11.86 (s, 1H) 1362. Et Cl H S CHMe 1363. Et Cl H SO CHMe 1364. Et Cl H SO₂ CHMe 1365. Et Cl H S C(CH₃)₂ 1366. Et Cl H SO C(CH₃)₂ 1367. Et Cl H SO₂ C(CH₃)₂ 1368. Et Cl H S C(OC₂H₄O) 1369. Et Cl H SO C(OC₂H₄O) 1370. Et Cl H SO₂ C(OC₂H₄O) 1371. Et Cl H S C(SC₂H₄S) 1372. Et Cl H SO C(SC₂H₄S) 1373. Et Cl H SO₂ C(SC₂H₄S) 1374. Et Cl H S CHOMe 1375. Et Cl H SO CHOMe 1376. Et Cl H SO₂ CHOMe CDCl3, 400 MHz: 1.62 (t, 3H), 3.55 (s, 3H), 3.66 (dd, 1H), 3.81 (d, 1H), 4.47 (q, 2H), 5.23 (d, 1H), 7.75 (d, 1H), 7.94 (d, 1H), 10.6 (s, 1H) 1377. Et Cl H S CHOEt 1378. Et Cl H SO CHOEt 1379. Et Cl H SO₂ CHOEt 1380. Et Cl H S CHOiPr 1381. Et Cl H SO CHOiPr 1382. Et Cl H SO₂ CHOiPr 1383. Et Cl H S CHOCH₂cPr 1384. Et Cl H SO CHOCH₂cPr 1385. Et Cl H SO₂ CHOCH₂cPr 1386. Et Cl H S CHOC₂H₄OMe 1387. Et Cl H SO CHOC₂H₄OMe 1388. Et Cl H SO₂ CHOC₂H₄OMe 1389. Et Cl H S CHOCH₂CCH 1390. Et Cl H SO CHOCH₂CCH 1391. Et Cl H SO₂ CHOCH₂CCH 1392. Et Cl H S CHOCH₂CH═CH₂ 1393. Et Cl H SO CHOCH₂CH═CH₂ 1394. Et Cl H SO₂ CHOCH₂CH═CH₂ 1395. Et Cl H S

1396. Et Cl H SO

1397. Et Cl H SO₂

1398. Et Cl H S

1399. Et Cl H SO

1400. Et Cl H SO₂

1401. Et Cl H S

1402. Et Cl H SO

1403. Et Cl H SO₂

1404. Et Cl H S

1405. Et Cl H SO

1406. Et Cl H SO₂

1407. Et Cl H S

1408. Et Cl H SO

1409. Et Cl H SO₂

1410. Et Cl H S CHOC₂H₄F 1411. Et Cl H SO CHOC₂H₄F 1412. Et Cl H SO₂ CHOC₂H₄F 1413. Et Cl H S C═NOMe 1414. Et Cl H SO C═NOMe 1415. Et Cl H SO₂ C═NOMe 1416. Et Cl H S C═NOCH₂CCH 1417. Et Cl H SO C═NOCH₂CCH 1418. Et Cl H SO₂ C═NOCH₂CCH 1419. Et Cl H S C═NOCH₂CH═CH₂ 1420. Et Cl H SO C═NOCH₂CH═CH₂ 1421. Et Cl H SO₂ C═NOCH₂CH═CH₂ 1422. Et Cl H S C═O 1423. Et Cl H SO C═O 1424. Et Cl H SO₂ C═O 1425. Et Cl H S C═S 1426. Et Cl H SO C═S 1427. Et Cl H SO₂ C═S 1428. Et Cl H S C═S 1429. Et Cl H SO C═S 1430. Et Cl H SO₂ C═S 1431. Et Cl H S C═N—N(CH₃)₂ 1432. Et Cl H SO C═N—N(CH₃)₂ 1433. Et Cl H SO₂ C═N—N(CH₃)₂ 1434. Et Cl H S O 1435. Et Cl H SO O 1436. Et Cl H SO₂ O 1437. Et Cl H S S 1438. Et Cl H SO S 1439. Et Cl H SO₂ S 1440. Et Cl H S SO 1441. Et Cl H SO SO 1442. Et Cl H SO₂ SO 1443. Et Cl H S SO₂ 1444. Et Cl H SO SO₂ 1445. Et Cl H SO₂ SO₂ 1446. Et Cl H S NMe 1447. Et Cl H SO NMe 1448. Et Cl H SO₂ NMe

TABLE 5 Inventive compounds of the general formula (I) in which Q is Q2, R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ Y X 1H NMR 1449. Me Me Me S CH₂ 1450. Me Me Me SO CH₂ 1451. Me Me Me SO₂ CH₂ 1452. Me Me Me S CHMe 1453. Me Me Me SO CHMe 1454. Me Me Me SO₂ CHMe 1455. Me Me Me S C(CH₃)₂ 1456. Me Me Me SO C(CH₃)₂ 1457. Me Me Me SO₂ C(CH₃)₂ 1458. Me Me Me S C(OC₂H₄O) 1459. Me Me Me SO C(OC₂H₄O) 1460. Me Me Me SO₂ C(OC₂H₄O) 1461. Me Me Me S C(SC₂H₄S) 1462. Me Me Me SO C(SC₂H₄S) 1463. Me Me Me SO₂ C(SC₂H₄S) 1464. Me Me Me S CHOMe 1465. Me Me Me SO CHOMe 1466. Me Me Me SO₂ CHOMe 1467. Me Me Me S CHOEt 1468. Me Me Me SO CHOEt 1469. Me Me Me SO₂ CHOEt 1470. Me Me Me S CHOiPr 1471. Me Me Me SO CHOiPr 1472. Me Me Me SO₂ CHOiPr 1473. Me Me Me S CHOCH₂cPr 1474. Me Me Me SO CHOCH₂cPr 1475. Me Me Me SO₂ CHOCH₂cPr 1476. Me Me Me S CHOC₂H₄OMe 1477. Me Me Me SO CHOC₂H₄OMe 1478. Me Me Me SO₂ CHOC₂H₄OMe 1479. Me Me Me S CHOCH₂CCH 1480. Me Me Me SO CHOCH₂CCH 1481. Me Me Me SO₂ CHOCH₂CCH 1482. Me Me Me S CHOCH₂CH═CH₂ 1483. Me Me Me SO CHOCH₂CH═CH₂ 1484. Me Me Me SO₂ CHOCH₂CH═CH₂ 1485. Me Me Me S

1486. Me Me Me SO

1487. Me Me Me SO₂

1488. Me Me Me S

1489. Me Me Me SO

1490. Me Me Me SO₂

1491. Me Me Me S

1492. Me Me Me SO

1493. Me Me Me SO₂

1494. Me Me Me S

1495. Me Me Me SO

1496. Me Me Me SO₂

1497. Me Me Me S

1498. Me Me Me SO

1499. Me Me Me SO₂

1500. Me Me Me S CHOC₂H₄F 1501. Me Me Me SO CHOC₂H₄F 1502. Me Me Me SO₂ CHOC₂H₄F 1503. Me Me Me S C═NOMe 1504. Me Me Me SO C═NOMe 1505. Me Me Me SO₂ C═NOMe 1506. Me Me Me S C═NOCH₂CCH 1507. Me Me Me SO C═NOCH₂CCH 1508. Me Me Me SO₂ C═NOCH₂CCH 1509. Me Me Me S C═NOCH₂CH═CH₂ 1510. Me Me Me SO C═NOCH₂CH═CH₂ 1511. Me Me Me SO₂ C═NOCH₂CH═CH₂ 1512. Me Me Me S C═O 1513. Me Me Me SO C═O 1514. Me Me Me SO₂ C═O 1515. Me Me Me S C═S 1516. Me Me Me SO C═S 1517. Me Me Me SO₂ C═S 1518. Me Me Me S C═S 1519. Me Me Me SO C═S 1520. Me Me Me SO₂ C═S 1521. Me Me Me S C═N—N(CH₃)₂ 1522. Me Me Me SO C═N—N(CH₃)₂ 1523. Me Me Me SO₂ C═N—N(CH₃)₂ 1524. Me Me Me S O 1525. Me Me Me SO O 1526. Me Me Me SO₂ O 1527. Me Me Me S S 1528. Me Me Me SO S 1529. Me Me Me SO₂ S 1530. Me Me Me S SO 1531. Me Me Me SO SO 1532. Me Me Me SO₂ SO 1533. Me Me Me S SO₂ 1534. Me Me Me SO SO₂ 1535. Me Me Me SO₂ SO₂ 1536. Me Me Me S NMe 1537. Me Me Me SO NMe 1538. Me Me Me SO₂ NMe 1539. Me Me Me O O 1540. Me Me H O O 1541. Me SMe H O O 1542. Me Cl H O O 1543. Me Cl H S CH₂ 1544. Me Cl H SO CH₂ 1545. Me Cl H SO₂ CH₂ DMSO, 400 MHz: 3.40 (t, 2H), 3.74 (t, 2H), 3.79 (s, 3H), 7.89 (br, 3H), 11.39 (s, 1H) 1546. Me Cl H S CHMe 1547. Me Cl H SO CHMe 1548. Me Cl H SO₂ CHMe 1549. Me Cl H S C(CH₃)₂ 1550. Me Cl H SO C(CH₃)₂ 1551. Me Cl H SO₂ C(CH₃)₂ 1552. Me Cl H S C(OC₂H₄O) 1553. Me Cl H SO C(OC₂H₄O) 1554. Me Cl H SO₂ C(OC₂H₄O) 1555. Me Cl H S C(SC₂H₄S) 1556. Me Cl H SO C(SC₂H₄S) 1557. Me Cl H SO₂ C(SC₂H₄S) 1558. Me Cl H S CHOMe 1559. Me Cl H SO CHOMe 1560. Me Cl H SO₂ CHOMe CDCl3, 400 MHz: 3.56 (s, 3H), 3.68 (dd, 1H), 3.71 (d, 1H), 3.87 (s, 3H), 5.21 (d, 1H), 7.64 (s, 1H), 7.73 (d, 1H), 7.91 (d, 1H), 9.85 (s, 1H) 1561. Me Cl H S CHOEt 1562. Me Cl H SO CHOEt 1563. Me Cl H SO₂ CHOEt 1564. Me Cl H S CHOiPr 1565. Me Cl H SO CHOiPr 1566. Me Cl H SO₂ CHOiPr 1567. Me Cl H S CHOCH₂cPr 1568. Me Cl H SO CHOCH₂cPr 1569. Me Cl H SO₂ CHOCH₂cPr 1570. Me Cl H S CHOC₂H₄OMe 1571. Me Cl H SO CHOC₂H₄OMe 1572. Me Cl H SO₂ CHOC₂H₄OMe 1573. Me Cl H S CHOCH₂CCH 1574. Me Cl H SO CHOCH₂CCH 1575. Me Cl H SO₂ CHOCH₂CCH 1576. Me Cl H S CHOCH₂CH═CH₂ 1577. Me Cl H SO CHOCH₂CH═CH₂ 1578. Me Cl H SO₂ CHOCH₂CH═CH₂ 1579. Me Cl H S

1580. Me Cl H SO

1581. Me Cl H SO₂

1582. Me Cl H S

1583. Me Cl H SO

1584. Me Cl H SO₂

1585. Me Cl H S

1586. Me Cl H SO

1587. Me Cl H SO₂

1588. Me Cl H S

1589. Me Cl H SO

1590. Me Cl H SO₂

1591. Me Cl H S

1592. Me Cl H SO

1593. Me Cl H SO₂

1594. Me Cl H S CHOC₂H₄F 1595. Me Cl H SO CHOC₂H₄F 1596. Me Cl H SO₂ CHOC₂H₄F 1597. Me Cl H S C═NOMe 1598. Me Cl H SO C═NOMe 1599. Me Cl H SO₂ C═NOMe 1600. Me Cl H S C═NOCH₂CCH 1601. Me Cl H SO C═NOCH₂CCH 1602. Me Cl H SO₂ C═NOCH₂CCH 1603. Me Cl H S C═NOCH₂CH═CH₂ 1604. Me Cl H SO C═NOCH₂CH═CH₂ 1605. Me Cl H SO₂ C═NOCH₂CH═CH₂ 1606. Me Cl H S C═O 1607. Me Cl H SO C═O 1608. Me Cl H SO₂ C═O 1609. Me Cl H S C═S 1610. Me Cl H SO C═S 1611. Me Cl H SO₂ C═S 1612. Me Cl H S C═S 1613. Me Cl H SO C═S 1614. Me Cl H SO₂ C═S 1615. Me Cl H S C═N—N(CH₃)₂ 1616. Me Cl H SO C═N—N(CH₃)₂ 1617. Me Cl H SO₂ C═N—N(CH₃)₂ 1618. Me Cl H S O 1619. Me Cl H SO O 1620. Me Cl H SO₂ O 1621. Me Cl H S S 1622. Me Cl H SO S 1623. Me Cl H SO₂ S 1624. Me Cl H S SO 1625. Me Cl H SO SO 1626. Me Cl H SO₂ SO 1627. Me Cl H S SO₂ 1628. Me Cl H SO SO₂ 1629. Me Cl H SO₂ SO₂ 1630. Me Cl H S NMe 1631. Me Cl H SO NMe 1632. Me Cl H SO₂ NMe 1633. Et Me Me S CH₂ 1634. Et Me Me SO CH₂ 1635. Et Me Me SO₂ CH₂ 1636. Et Me Me S CHMe 1637. Et Me Me SO CHMe 1638. Et Me Me SO₂ CHMe 1639. Et Me Me S C(CH₃)₂ 1640. Et Me Me SO C(CH₃)₂ 1641. Et Me Me SO₂ C(CH₃)₂ 1642. Et Me Me S C(OC₂H₄O) 1643. Et Me Me SO C(OC₂H₄O) 1644. Et Me Me SO₂ C(OC₂H₄O) 1645. Et Me Me S C(SC₂H₄S) 1646. Et Me Me SO C(SC₂H₄S) 1647. Et Me Me SO₂ C(SC₂H₄S) 1648. Et Me Me S CHOMe 1649. Et Me Me SO CHOMe 1650. Et Me Me SO₂ CHOMe 1651. Et Me Me S CHOEt 1652. Et Me Me SO CHOEt 1653. Et Me Me SO₂ CHOEt 1654. Et Me Me S CHOiPr 1655. Et Me Me SO CHOiPr 1656. Et Me Me SO₂ CHOiPr 1657. Et Me Me S CHOCH₂cPr 1658. Et Me Me SO CHOCH₂cPr 1659. Et Me Me SO₂ CHOCH₂cPr 1660. Et Me Me S CHOC₂H₄OMe 1661. Et Me Me SO CHOC₂H₄OMe 1662. Et Me Me SO₂ CHOC₂H₄OMe 1663. Et Me Me S CHOCH₂CCH 1664. Et Me Me SO CHOCH₂CCH 1665. Et Me Me SO₂ CHOCH₂CCH 1666. Et Me Me S CHOCH₂CH═CH₂ 1667. Et Me Me SO CHOCH₂CH═CH₂ 1668. Et Me Me SO₂ CHOCH₂CH═CH₂ 1669. Et Me Me S

1670. Et Me Me SO

1671. Et Me Me SO₂

1672. Et Me Me S

1673. Et Me Me SO

1674. Et Me Me SO₂

1675. Et Me Me S

1676. Et Me Me SO

1677. Et Me Me SO₂

1678. Et Me Me S

1679. Et Me Me SO

1680. Et Me Me SO₂

1681. Et Me Me S

1682. Et Me Me SO

1683. Et Me Me SO₂

1684. Et Me Me S CHOC₂H₄F 1685. Et Me Me SO CHOC₂H₄F 1686. Et Me Me SO₂ CHOC₂H₄F 1687. Et Me Me S C═NOMe 1688. Et Me Me SO C═NOMe 1689. Et Me Me SO₂ C═NOMe 1690. Et Me Me S C═NOCH₂CCH 1691. Et Me Me SO C═NOCH₂CCH 1692. Et Me Me SO₂ C═NOCH₂CCH 1693. Et Me Me S C═NOCH₂CH═CH₂ 1694. Et Me Me SO C═NOCH₂CH═CH₂ 1695. Et Me Me SO₂ C═NOCH₂CH═CH₂ 1696. Et Me Me S C═O 1697. Et Me Me SO C═O 1698. Et Me Me SO₂ C═O 1699. Et Me Me S C═S 1700. Et Me Me SO C═S 1701. Et Me Me SO₂ C═S 1702. Et Me Me S C═S 1703. Et Me Me SO C═S 1704. Et Me Me SO₂ C═S 1705. Et Me Me S C═N—N(CH₃)₂ 1706. Et Me Me SO C═N—N(CH₃)₂ 1707. Et Me Me SO₂ C═N—N(CH₃)₂ 1708. Et Me Me S O 1709. Et Me Me SO O 1710. Et Me Me SO₂ O 1711. Et Me Me S S 1712. Et Me Me SO S 1713. Et Me Me SO₂ S 1714. Et Me Me S SO 1715. Et Me Me SO SO 1716. Et Me Me SO₂ SO 1717. Et Me Me S SO₂ 1718. Et Me Me SO SO₂ 1719. Et Me Me SO₂ SO₂ 1720. Et Me Me S NMe 1721. Et Me Me SO NMe 1722. Et Me Me SO₂ NMe 1723. Et Me Me O O 1724. Et Me H O O 1725. Et SMe H O O 1726. Et Cl H O O 1727. Et Cl H S CH₂ 1728. Et Cl H SO CH₂ 1729. Et Cl H SO₂ CH₂ 1730. Et Cl H S CHMe 1731. Et Cl H SO CHMe 1732. Et Cl H SO₂ CHMe 1733. Et Cl H S C(CH₃)₂ 1734. Et Cl H SO C(CH₃)₂ 1735. Et Cl H SO₂ C(CH₃)₂ 1736. Et Cl H S C(OC₂H₄O) 1737. Et Cl H SO C(OC₂H₄O) 1738. Et Cl H SO₂ C(OC₂H₄O) 1739. Et Cl H S C(SC₂H₄S) 1740. Et Cl H SO C(SC₂H₄S) 1741. Et Cl H SO₂ C(SC₂H₄S) 1742. Et Cl H S CHOMe 1743. Et Cl H SO CHOMe 1744. Et Cl H SO₂ CHOMe 1745. Et Cl H S CHOEt 1746. Et Cl H SO CHOEt 1747. Et Cl H SO₂ CHOEt 1748. Et Cl H S CHOiPr 1749. Et Cl H SO CHOiPr 1750. Et Cl H SO₂ CHOiPr 1751. Et Cl H S CHOCH₂cPr 1752. Et Cl H SO CHOCH₂cPr 1753. Et Cl H SO₂ CHOCH₂cPr 1754. Et Cl H S CHOC₂H₄OMe 1755. Et Cl H SO CHOC₂H₄OMe 1756. Et Cl H SO₂ CHOC₂H₄OMe 1757. Et Cl H S CHOCH₂CCH 1758. Et Cl H SO CHOCH₂CCH 1759. Et Cl H SO₂ CHOCH₂CCH 1760. Et Cl H S CHOCH₂CH═CH₂ 1761. Et Cl H SO CHOCH₂CH═CH₂ 1762. Et Cl H SO₂ CHOCH₂CH═CH₂ 1763. Et Cl H S

1764. Et Cl H SO

1765. Et Cl H SO₂

1766. Et Cl H S

1767. Et Cl H SO

1768. Et Cl H SO₂

1769. Et Cl H S

1770. Et Cl H SO

1771. Et Cl H SO₂

1772. Et Cl H S

1773. Et Cl H SO

1774. Et Cl H SO₂

1775. Et Cl H S

1776. Et Cl H SO

1777. Et Cl H SO₂

1778. Et Cl H S CHOC₂H₄F 1779. Et Cl H SO CHOC₂H₄F 1780. Et Cl H SO₂ CHOC₂H₄F 1781. Et Cl H S C═NOMe 1782. Et Cl H SO C═NOMe 1783. Et Cl H SO₂ C═NOMe 1784. Et Cl H S C═NOCH₂CCH 1785. Et Cl H SO C═NOCH₂CCH 1786. Et Cl H SO₂ C═NOCH₂CCH 1787. Et Cl H S C═NOCH₂CH═CH₂ 1788. Et Cl H SO C═NOCH₂CH═CH₂ 1789. Et Cl H SO₂ C═NOCH₂CH═CH₂ 1790. Et Cl H S C═O 1791. Et Cl H SO C═O 1792. Et Cl H SO₂ C═O 1793. Et Cl H S C═S 1794. Et Cl H SO C═S 1795. Et Cl H SO₂ C═S 1796. Et Cl H S C═S 1797. Et Cl H SO C═S 1798. Et Cl H SO₂ C═S 1799. Et Cl H S C═N—N (CH₃)₂ 1800. Et Cl H SO C═N—N (CH₃)₂ 1801. Et Cl H SO₂ C═N—N (CH₃)₂ 1802. Et Cl H S O 1803. Et Cl H SO O 1804. Et Cl H SO₂ O 1805. Et Cl H S S 1806. Et Cl H SO S 1807. Et Cl H SO₂ S 1808. Et Cl H S SO 1809. Et Cl H SO SO 1810. Et Cl H SO₂ SO 1811. Et Cl H S SO₂ 1812. Et Cl H SO SO₂ 1813. Et Cl H SO₂ SO₂ 1814. Et Cl H S NMe 1815. Et Cl H SO NMe 1816. Et Cl H SO₂ NMe

TABLE 6 Inventive compounds of the general formula (I) in which Q is Q3, R⁵ is hydrogen and n is 1

No. R² R³ R⁴ Y X 1H NMR 1817. Me Me Me S CH₂ 1818. Me Me Me SO CH₂ 1819. Me Me Me SO₂ CH₂ 1820. Me Me Me S CHMe 1821. Me Me Me SO CHMe 1822. Me Me Me SO₂ CHMe 1823. Me Me Me S C(CH₃)₂ 1824. Me Me Me SO C(CH₃)₂ 1825. Me Me Me SO₂ C(CH₃)₂ 1826. Me Me Me S C(OC₂H₄O) 1827. Me Me Me SO C(OC₂H₄O) 1828. Me Me Me SO₂ C(OC₂H₄O) 1829. Me Me Me S C(SC₂H₄S) 1830. Me Me Me SO C(SC₂H₄S) 1831. Me Me Me SO₂ C(SC₂H₄S) 1832. Me Me Me S CHOMe 1833. Me Me Me SO CHOMe 1834. Me Me Me SO₂ CHOMe 1835. Me Me Me S CHOEt 1836. Me Me Me SO CHOEt 1837. Me Me Me SO₂ CHOEt 1838. Me Me Me S CHOiPr 1839. Me Me Me SO CHOiPr 1840. Me Me Me SO₂ CHOiPr 1841. Me Me Me S CHOCH₂cPr 1842. Me Me Me SO CHOCH₂cPr 1843. Me Me Me SO₂ CHOCH₂cPr 1844. Me Me Me S CHOC₂H₄OMe 1845. Me Me Me SO CHOC₂H₄OMe 1846. Me Me Me SO₂ CHOC₂H₄OMe 1847. Me Me Me S CHOCH₂CCH 1848. Me Me Me SO CHOCH₂CCH 1849. Me Me Me SO₂ CHOCH₂CCH 1850. Me Me Me S CHOCH₂CH═CH₂ 1851. Me Me Me SO CHOCH₂CH═CH₂ 1852. Me Me Me SO₂ CHOCH₂CH═CH₂ 1853. Me Me Me S

1854. Me Me Me SO

1855. Me Me Me SO₂

1856. Me Me Me S

1857. Me Me Me SO

1858. Me Me Me SO₂

1859. Me Me Me S

1860. Me Me Me SO

1861. Me Me Me SO₂

1862. Me Me Me S

1863. Me Me Me SO

1864. Me Me Me SO₂

1865. Me Me Me S

1866. Me Me Me SO

1867. Me Me Me SO₂

1868. Me Me Me S CHOC₂H₄F 1869. Me Me Me SO CHOC₂H₄F 1870. Me Me Me SO₂ CHOC₂H₄F 1871. Me Me Me S C═NOMe 1872. Me Me Me SO C═NOMe 1873. Me Me Me SO₂ C═NOMe 1874. Me Me Me S C═NOCH₂CCH 1875. Me Me Me SO C═NOCH₂CCH 1876. Me Me Me SO₂ C═NOCH₂CCH 1877. Me Me Me S C═NOCH₂CH═CH₂ 1878. Me Me Me SO C═NOCH₂CH═CH₂ 1879. Me Me Me SO₂ C═NOCH₂CH═CH₂ 1880. Me Me Me S C═O 1881. Me Me Me SO C═O 1882. Me Me Me SO₂ C═O 1883. Me Me Me S C═S 1884. Me Me Me SO C═S 1885. Me Me Me SO₂ C═S 1886. Me Me Me S C═S 1887. Me Me Me SO C═S 1888. Me Me Me SO₂ C═S 1889. Me Me Me S C═N—N(CH₃)₂ 1890. Me Me Me SO C═N—N(CH₃)₂ 1891. Me Me Me SO₂ C═N—N(CH₃)₂ 1892. Me Me Me S O 1893. Me Me Me SO O 1894. Me Me Me SO₂ O 1895. Me Me Me S S 1896. Me Me Me SO S 1897. Me Me Me SO₂ S 1898. Me Me Me S SO 1899. Me Me Me SO SO 1900. Me Me Me SO₂ SO 1901. Me Me Me S SO₂ 1902. Me Me Me SO SO₂ 1903. Me Me Me SO₂ SO₂ 1904. Me Me Me S NMe 1905. Me Me Me SO NMe 1906. Me Me Me SO₂ NMe 1907. Me Me Me O O 1908. Me Me H O O 1909. Me SMe H O O 1910. Me Cl H O O 1911. Me Cl H S CH₂ 1912. Me Cl H SO CH₂ 1913. Me Cl H SO₂ CH₂ CDCl3, 400 MHz: 2.52 (s, 3H), 3.47 (t, 2H), 3.62 (t, 2H), 3.79 (s, 3H), 7.80 (d, 1H), 7.88 (d, 1H), 8.14 (s, 1H) 1914. Me Cl H S CHMe 1915. Me Cl H SO CHMe 1916. Me Cl H SO₂ CHMe 1917. Me Cl H S C(CH₃)₂ 1918. Me Cl H SO C(CH₃)₂ 1919. Me Cl H SO₂ C(CH₃)₂ 1920. Me Cl H S C(OC₂H₄O) 1921. Me Cl H SO C(OC₂H₄O) 1922. Me Cl H SO₂ C(OC₂H₄O) 1923. Me Cl H S C(SC₂H₄S) 1924. Me Cl H SO C(SC₂H₄S) 1925. Me Cl H SO₂ C(SC₂H₄S) 1926. Me Cl H S CHOMe 1927. Me Cl H SO CHOMe 1928. Me Cl H SO₂ CHOMe CDCl3, 400 MHz: 2.44 (s, 3H), 3.53 (s, 3H), 3.57 (dd, 1H), 3.71 (d, 1H), 5.15 (d, 1H), 7.55 (d, 1H), 7.74 (d, 1H), 9.40 (s, 1H) 1929. Me Cl H S CHOEt 1930. Me Cl H SO CHOEt 1931. Me Cl H SO₂ CHOEt 1932. Me Cl H S CHOiPr 1933. Me Cl H SO CHOiPr 1934. Me Cl H SO₂ CHOiPr 1935. Me Cl H S CHOCH₂cPr 1936. Me Cl H SO CHOCH₂cPr 1937. Me Cl H SO₂ CHOCH₂cPr 1938. Me Cl H S CHOC₂H₄OMe 1939. Me Cl H SO CHOC₂H₄OMe 1940. Me Cl H SO₂ CHOC₂H₄OMe 1941. Me Cl H S CHOCH₂CCH 1942. Me Cl H SO CHOCH₂CCH 1943. Me Cl H SO₂ CHOCH₂CCH 1944. Me Cl H S CHOCH₂CH═CH₂ 1945. Me Cl H SO CHOCH₂CH═CH₂ 1946. Me Cl H SO₂ CHOCH₂CH═CH₂ 1947. Me Cl H S

1948. Me Cl H SO

1949. Me Cl H SO₂

1950. Me Cl H S

1951. Me Cl H SO

1952. Me Cl H SO₂

1953. Me Cl H S

1954. Me Cl H SO

1955. Me Cl H SO₂

1956. Me Cl H S

1957. Me Cl H SO

1958. Me Cl H SO₂

1959. Me Cl H S

1960. Me Cl H SO

1961. Me Cl H SO₂

1962. Me Cl H S CHOC₂H₄F 1963. Me Cl H SO CHOC₂H₄F 1964. Me Cl H SO₂ CHOC₂H₄F 1965. Me Cl H S C═NOMe 1966. Me Cl H SO C═NOMe 1967. Me Cl H SO₂ C═NOMe 1968. Me Cl H S C═NOCH₂CCH 1969. Me Cl H SO C═NOCH₂CCH 1970. Me Cl H SO₂ C═NOCH₂CCH 1971. Me Cl H S C═NOCH₂CH═CH₂ 1972. Me Cl H SO C═NOCH₂CH═CH₂ 1973. Me Cl H SO₂ C═NOCH₂CH═CH₂ 1974. Me Cl H S C═O 1975. Me Cl H SO C═O 1976. Me Cl H SO₂ C═O 1977. Me Cl H S C═S 1978. Me Cl H SO C═S 1979. Me Cl H SO₂ C═S 1980. Me Cl H S C═S 1981. Me Cl H SO C═S 1982. Me Cl H SO₂ C═S 1983. Me Cl H S C═N—N(CH₃)₂ 1984. Me Cl H SO C═N—N(CH₃)₂ 1985. Me Cl H SO₂ C═N—N(CH₃)₂ 1986. Me Cl H S O 1987. Me Cl H SO O 1988. Me Cl H SO₂ O 1989. Me Cl H S S 1990. Me Cl H SO S 1991. Me Cl H SO₂ S 1992. Me Cl H S SO 1993. Me Cl H SO SO 1994. Me Cl H SO₂ SO 1995. Me Cl H S SO₂ 1996. Me Cl H SO SO₂ 1997. Me Cl H SO₂ SO₂ 1998. Me Cl H S NMe 1999. Me Cl H SO NMe 2000. Me Cl H SO₂ NMe 2001. Et Me Me S CH₂ 2002. Et Me Me SO CH₂ 2003. Et Me Me SO₂ CH₂ 2004. Et Me Me S CHMe 2005. Et Me Me SO CHMe 2006. Et Me Me SO₂ CHMe 2007. Et Me Me S C(CH₃)₂ 2008. Et Me Me SO C(CH₃)₂ 2009. Et Me Me SO₂ C(CH₃)₂ 2010. Et Me Me S C(OC₂H₄O) 2011. Et Me Me SO C(OC₂H₄O) 2012. Et Me Me SO₂ C(OC₂H₄O) 2013. Et Me Me S C(SC₂H₄S) 2014. Et Me Me SO C(SC₂H₄S) 2015. Et Me Me SO₂ C(SC₂H₄S) 2016. Et Me Me S CHOMe 2017. Et Me Me SO CHOMe 2018. Et Me Me SO₂ CHOMe 2019. Et Me Me S CHOEt 2020. Et Me Me SO CHOEt 2021. Et Me Me SO₂ CHOEt 2022. Et Me Me S CHOiPr 2023. Et Me Me SO CHOiPr 2024. Et Me Me SO₂ CHOiPr 2025. Et Me Me S CHOCH₂cPr 2026. Et Me Me SO CHOCH₂cPr 2027. Et Me Me SO₂ CHOCH₂cPr 2028. Et Me Me S CHOC₂H₄OMe 2029. Et Me Me SO CHOC₂H₄OMe 2030. Et Me Me SO₂ CHOC₂H₄OMe 2031. Et Me Me S CHOCH₂CCH 2032. Et Me Me SO CHOCH₂CCH 2033. Et Me Me SO₂ CHOCH₂CCH 2034. Et Me Me S CHOCH₂CH═CH₂ 2035. Et Me Me SO CHOCH₂CH═CH₂ 2036. Et Me Me SO₂ CHOCH₂CH═CH₂ 2037. Et Me Me S

2038. Et Me Me SO

2039. Et Me Me SO₂

2040. Et Me Me S

2041. Et Me Me SO

2042. Et Me Me SO₂

2043. Et Me Me S

2044. Et Me Me SO

2045. Et Me Me SO₂

2046. Et Me Me S

2047. Et Me Me SO

2048. Et Me Me SO₂

2049. Et Me Me S

2050. Et Me Me SO

2051. Et Me Me SO₂

2052. Et Me Me S CHOC₂H₄F 2053. Et Me Me SO CHOC₂H₄F 2054. Et Me Me SO₂ CHOC₂H₄F 2055. Et Me Me S C═NOMe 2056. Et Me Me SO C═NOMe 2057. Et Me Me SO₂ C═NOMe 2058. Et Me Me S C═NOCH₂CCH 2059. Et Me Me SO C═NOCH₂CCH 2060. Et Me Me SO₂ C═NOCH₂CCH 2061. Et Me Me S C═NOCH₂CH═CH₂ 2062. Et Me Me SO C═NOCH₂CH═CH₂ 2063. Et Me Me SO₂ C═NOCH₂CH═CH₂ 2064. Et Me Me S C═O 2065. Et Me Me SO C═O 2066. Et Me Me SO₂ C═O 2067. Et Me Me S C═S 2068. Et Me Me SO C═S 2069. Et Me Me SO₂ C═S 2070. Et Me Me S C═S 2071. Et Me Me SO C═S 2072. Et Me Me SO₂ C═S 2073. Et Me Me S C═N—N(CH₃)₂ 2074. Et Me Me SO C═N—N(CH₃)₂ 2075. Et Me Me SO₂ C═N—N(CH₃)₂ 2076. Et Me Me S O 2077. Et Me Me SO O 2078. Et Me Me SO₂ O 2079. Et Me Me S S 2080. Et Me Me SO S 2081. Et Me Me SO₂ S 2082. Et Me Me S SO 2083. Et Me Me SO SO 2084. Et Me Me SO₂ SO 2085. Et Me Me S SO₂ 2086. Et Me Me SO SO₂ 2087. Et Me Me SO₂ SO₂ 2088. Et Me Me S NMe 2089. Et Me Me SO NMe 2090. Et Me Me SO₂ NMe 2091. Et Me Me O O 2092. Et Me H O O 2093. Et SMe H O O 2094. Et Cl H O O 2095. Et Cl H S CH₂ 2096. Et Cl H SO CH₂ 2097. Et Cl H SO₂ CH₂ 2098. Et Cl H S CHMe 2099. Et Cl H SO CHMe 2100. Et Cl H SO₂ CHMe 2101. Et Cl H S C(CH₃)₂ 2102. Et Cl H SO C(CH₃)₂ 2103. Et Cl H SO₂ C(CH₃)₂ 2104. Et Cl H S C(OC₂H₄O) 2105. Et Cl H SO C(OC₂H₄O) 2106. Et Cl H SO₂ C(OC₂H₄O) 2107. Et Cl H S C(SC₂H₄S) 2108. Et Cl H SO C(SC₂H₄S) 2109. Et Cl H SO₂ C(SC₂H₄S) 2110. Et Cl H S CHOMe 2111. Et Cl H SO CHOMe 2112. Et Cl H SO₂ CHOMe 2113. Et Cl H S CHOEt 2114. Et Cl H SO CHOEt 2115. Et Cl H SO₂ CHOEt 2116. Et Cl H S CHOiPr 2117. Et Cl H SO CHOiPr 2118. Et Cl H SO₂ CHOiPr 2119. Et Cl H S CHOCH₂cPr 2120. Et Cl H SO CHOCH₂cPr 2121. Et Cl H SO₂ CHOCH₂cPr 2122. Et Cl H S CHOC₂H₄OMe 2123. Et Cl H SO CHOC₂H₄OMe 2124. Et Cl H SO₂ CHOC₂H₄OMe 2125. Et Cl H S CHOCH₂CCH 2126. Et Cl H SO CHOCH₂CCH 2127. Et Cl H SO₂ CHOCH₂CCH 2128. Et Cl H S CHOCH₂CH═CH₂ 2129. Et Cl H SO CHOCH₂CH═CH₂ 2130. Et Cl H SO₂ CHOCH₂CH═CH₂ 2131. Et Cl H S

2132. Et Cl H SO

2133. Et Cl H SO₂

2134. Et Cl H S

2135. Et Cl H SO

2136. Et Cl H SO₂

2137. Et Cl H S

2138. Et Cl H SO

2139. Et Cl H SO₂

2140. Et Cl H S

2141. Et Cl H SO

2142. Et Cl H SO₂

2143. Et Cl H S

2144. Et Cl H SO

2145. Et Cl H SO₂

2146. Et Cl H S CHOC₂H₄F 2147. Et Cl H SO CHOC₂H₄F 2148. Et Cl H SO₂ CHOC₂H₄F 2149. Et Cl H S C═NOMe 2150. Et Cl H SO C═NOMe 2151. Et Cl H SO₂ C═NOMe 2152. Et Cl H S C═NOCH₂CCH 2153. Et Cl H SO C═NOCH₂CCH 2154. Et Cl H SO₂ C═NOCH₂CCH 2155. Et Cl H S C═NOCH₂CH═CH₂ 2156. Et Cl H SO C═NOCH₂CH═CH₂ 2157. Et Cl H SO₂ C═NOCH₂CH═CH₂ 2158. Et Cl H S C═O 2159. Et Cl H SO C═O 2160. Et Cl H SO₂ C═O 2161. Et Cl H S C═S 2162. Et Cl H SO C═S 2163. Et Cl H SO₂ C═S 2164. Et Cl H S C═S 2165. Et Cl H SO C═S 2166. Et Cl H SO₂ C═S 2167. Et Cl H S C═N—N(CH₃)₂ 2168. Et Cl H SO C═N—N(CH₃)₂ 2169. Et Cl H SO₂ C═N—N(CH₃)₂ 2170. Et Cl H S O 2171. Et Cl H SO O 2172. Et Cl H SO₂ O 2173. Et Cl H S S 2174. Et Cl H SO S 2175. Et Cl H SO₂ S 2176. Et Cl H S SO 2177. Et Cl H SO SO 2178. Et Cl H SO₂ SO 2179. Et Cl H S SO₂ 2180. Et Cl H SO SO₂ 2181. Et Cl H SO₂ SO₂ 2182. Et Cl H S NMe 2183. Et Cl H SO NMe 2184. Et Cl H SO₂ NMe

TABLE 7 Inventive compounds of the general formula (I) in which Q is Q1, X and Y are each oxygen, R⁵ is fluorine and n is 1

No. R¹ R³ R⁴ 1H NMR 2185. Me Me Me 2186. Me Me H DMSO-d6, 400 MHz: 7.62 (d, 1H), 7.40 (d, 1H), 3.90 (s, 3H), 2.39 (s, 3H) 2187. Me Cl H 2188. Me SMe H 2189. Me Me Me 2190. Me Me H 2191. Me Cl H 2192. Me SMe H 2193. Et Me Me 2194. Et Me H 2195. Et Cl H 2196. Et SMe H 2197. Et Me Me 2198. Et Me H 2199. Et Cl H 2200. Et SMe H

TABLE 8 Inventive compounds of the general formula (I) in which Q is Q3, X is 2-(1,4-pyrazinyl)oxymethyl, Y is SO₂, R⁵ is hydrogen and n is 2

No. R² R³ R⁴ 1H NMR 2201. Cl Me Me 2202. Cl Me H 2203. Cl Cl H 2204. OMe Me Me DMSO-d₆, 400 MHz: 11.36 (s, 1H), 8.38 (s, 1H), 8.33-8.31 (m, 2H), 7.60 (s, 1H), 6.51 (dd, 1H), 4.07 (s, 3H), 3.77-3.70 (m, 1H), 3.58-3.53 (m, 1H), 2.76-2.60 (m, 5H), 2.18 (s, 3H) 2205. OMe Me H 2206. OMe Cl H 2207. NHAc Me Me 2208. NHAc Me H 2209. NHAc Cl H

TABLE 9 Inventive compounds of the general formula (I) in which Q is Q1, Y is SO₂, R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ X 1H NMR 2210. nPr Me Me CH₂ 2211. nPr Me H CH₂ 2212. nPr Cl H CH₂ DMSO-d₆, 400 MHz: 0.89 (t, 3H), 1.89 (m, 2H), 3.42 (t, 2H), 3.76 (t, 2H), 4.33 (t, 2H), 7.90 (d, 1H), 7.94 (d, 1H), 11.84 (s, 1H) 2213. C₂H₄OMe Me Me CH₂ 2214. C₂H₄OMe Me H CH₂ 2215. C₂H₄OMe Cl H CH₂ 2216. CH₂CF₃ Me Me CH₂ 2217. CH₂CF₃ Me H CH₂ 2218. CH₂CF₃ Cl H CH₂ 2219. nPr Me Me CHOMe 2220. nPr Me H CHOMe 2221. nPr Cl H CHOMe DMSO-d₆, 400 MHz: 0.99 (t, 3H), 2.01 (m, 2H), 3.53 (s, 3H), 3.63 (dd, 1H), 3.80 (d, 1H), 4.40 (t, 2H), 5.22 (d, 1H), 7.72 (d, 1H), 7.92 (d, 1H), 10.80 (s, 1H) 2222. C₂H₄OMe Me Me CHOMe 2223. C₂H₄OMe Me H CHOMe 2224. C₂H₄OMe Cl H CHOMe 2225. CH₂CF₃ Me Me CHOMe 2226. CH₂CF₃ Me H CHOMe 2227. CH₂CF₃ Cl H CHOMe

TABLE 10 Inventive compounds of the general formula (I) in which Q is Q1 and R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ X Y 1H NMR 2228. Me Me Me S C═O 2229. Me Me Me SO C═O 2230. Me Me Me SO₂ C═O 2231. Me Me Me S CHOMe 2232. Me Me Me SO CHOMe 2233. Me Me Me SO₂ CHOMe 2234. Me Me Me S CHOEt 2235. Me Me Me SO CHOEt 2236. Me Me Me SO₂ CHOEt 2237. Me Me Me S C═NOMe 2238. Me Me Me SO C═NOMe 2239. Me Me Me SO₂ C═NOMe 2240. Me Me Me S C═NOEt 2241. Me Me Me SO C═NOEt 2242. Me Me Me SO₂ C═NOEt 2243. Me Me Me S O 2244. Me Me Me SO O 2245. Me Me Me SO₂ O 2246. Me Me Me S S 2247. Me Me Me SO S 2248. Me Me Me SO₂ S 2249. Me Me Me S SO₂ 2250. Me Me Me SO SO₂ 2251. Me Me Me SO₂ SO₂ 2252. Me Me H S C═O 2253. Me Me H SO C═O 2254. Me Me H SO₂ C═O 2255. Me Me H S CHOMe 2256. Me Me H SO CHOMe 2257. Me Me H SO₂ CHOMe 2258. Me Me H S CHOEt 2259. Me Me H SO CHOEt 2260. Me Me H SO₂ CHOEt 2261. Me Me H S C═NOMe 2262. Me Me H SO C═NOMe 2263. Me Me H SO₂ C═NOMe 2264. Me Me H S C═NOEt 2265. Me Me H SO C═NOEt 2266. Me Me H SO₂ C═NOEt 2267. Me Me H S O 2268. Me Me H SO O 2269. Me Me H SO₂ O 2270. Me Me H S S 2271. Me Me H SO S 2272. Me Me H SO₂ S 2273. Me Me H S SO₂ 2274. Me Me H SO SO₂ 2275. Me Me H SO₂ SO₂

TABLE 11 Inventive compounds of the general formula (I) in which Q is Q2, R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ X Y 1H NMR 2276. Me Me Me S C═O 2277. Me Me Me SO C═O 2278. Me Me Me SO₂ C═O 2279. Me Me Me S CHOMe 2280. Me Me Me SO CHOMe 2281. Me Me Me SO₂ CHOMe 2282. Me Me Me S CHOEt 2283. Me Me Me SO CHOEt 2284. Me Me Me SO₂ CHOEt 2285. Me Me Me S C═NOMe 2286. Me Me Me SO C═NOMe 2287. Me Me Me SO₂ C═NOMe 2288. Me Me Me S C═NOEt 2289. Me Me Me SO C═NOEt 2290. Me Me Me SO₂ C═NOEt 2291. Me Me Me S O 2292. Me Me Me SO O 2293. Me Me Me SO₂ O 2294. Me Me Me S S 2295. Me Me Me SO S 2296. Me Me Me SO₂ S 2297. Me Me Me S SO₂ 2298. Me Me Me SO SO₂ 2299. Me Me Me SO₂ SO₂ 2300. Me Me H S C═O 2301. Me Me H SO C═O 2302. Me Me H SO₂ C═O 2303. Me Me H S CHOMe 2304. Me Me H SO CHOMe 2305. Me Me H SO₂ CHOMe 2306. Me Me H S CHOEt 2307. Me Me H SO CHOEt 2308. Me Me H SO₂ CHOEt 2309. Me Me H S C═NOMe 2310. Me Me H SO C═NOMe 2311. Me Me H SO₂ C═NOMe 2312. Me Me H S C═NOEt 2313. Me Me H SO C═NOEt 2314. Me Me H SO₂ C═NOEt 2315. Me Me H S O 2316. Me Me H SO O 2317. Me Me H SO₂ O 2318. Me Me H S S 2319. Me Me H SO S 2320. Me Me H SO₂ S 2321. Me Me H S SO₂ 2322. Me Me H SO SO₂ 2323. Me Me H SO₂ SO₂

TABLE 12 Inventive compounds of the general formula (I) in which Q is Q3, R⁵ is hydrogen and n is 1

No. R² R³ R⁴ X Y 1H NMR 2324. Me Me Me S C═O 2325. Me Me Me SO C═O 2326. Me Me Me SO₂ C═O 2327. Me Me Me S CHOMe 2328. Me Me Me SO CHOMe 2329. Me Me Me SO₂ CHOMe 2330. Me Me Me S CHOEt 2331. Me Me Me SO CHOEt 2332. Me Me Me SO₂ CHOEt 2333. Me Me Me S C═NOMe 2334. Me Me Me SO C═NOMe 2335. Me Me Me SO₂ C═NOMe 2336. Me Me Me S C═NOEt 2337. Me Me Me SO C═NOEt 2338. Me Me Me SO₂ C═NOEt 2339. Me Me Me S O 2340. Me Me Me SO O 2341. Me Me Me SO₂ O 2342. Me Me Me S S 2343. Me Me Me SO S 2344. Me Me Me SO₂ S 2345. Me Me Me S SO₂ 2346. Me Me Me SO SO₂ 2347. Me Me Me SO₂ SO₂ 2348. Me Me H S C═O 2349. Me Me H SO C═O 2350. Me Me H SO₂ C═O 2351. Me Me H S CHOMe 2352. Me Me H SO CHOMe 2353. Me Me H SO₂ CHOMe 2354. Me Me H S CHOEt 2355. Me Me H SO CHOEt 2356. Me Me H SO₂ CHOEt 2357. Me Me H S C═NOMe 2358. Me Me H SO C═NOMe 2359. Me Me H SO₂ C═NOMe 2360. Me Me H S C═NOEt 2361. Me Me H SO C═NOEt 2362. Me Me H SO₂ C═NOEt 2363. Me Me H S O 2364. Me Me H SO O 2365. Me Me H SO₂ O 2366. Me Me H S S 2367. Me Me H SO S 2368. Me Me H SO₂ S 2369. Me Me H S SO₂ 2370. Me Me H SO SO₂ 2371. Me Me H SO₂ SO₂

TABLE 13 Inventive compounds of the general formula (I) in which Q is Q1, R⁵ is hydrogen and n is 2

No. R¹ R³ R⁴ X Y 1H NMR 2372. Me Me Me S C═O 2373. Me Me Me SO C═O 2374. Me Me Me SO₂ C═O 2375. Me Me Me S CHOMe 2376. Me Me Me SO CHOMe 2377. Me Me Me SO₂ CHOMe 2378. Me Me Me S CHOEt 2379. Me Me Me SO CHOEt 2380. Me Me Me SO₂ CHOEt 2381. Me Me Me S C═NOMe 2382. Me Me Me SO C═NOMe 2383. Me Me Me SO₂ C═NOMe 2384. Me Me Me S C═NOEt 2385. Me Me Me SO C═NOEt 2386. Me Me Me SO₂ C═NOEt 2387. Me Me Me S O 2388. Me Me Me SO O 2389. Me Me Me SO₂ O 2390. Me Me Me S S 2391. Me Me Me SO S 2392. Me Me Me SO₂ S 2393. Me Me Me S SO₂ 2394. Me Me Me SO SO₂ 2395. Me Me Me SO₂ SO₂ 2396. Me Me H S C═O 2397. Me Me H SO C═O 2398. Me Me H SO₂ C═O 2399. Me Me H S CHOMe 2400. Me Me H SO CHOMe 2401. Me Me H SO₂ CHOMe 2402. Me Me H S CHOEt 2403. Me Me H SO CHOEt 2404. Me Me H SO₂ CHOEt 2405. Me Me H S C═NOMe 2406. Me Me H SO C═NOMe 2407. Me Me H SO₂ C═NOMe 2408. Me Me H S C═NOEt 2409. Me Me H SO C═NOEt 2410. Me Me H SO₂ C═NOEt 2411. Me Me H S O 2412. Me Me H SO O 2413. Me Me H SO₂ O 2414. Me Me H S S 2415. Me Me H SO S 2416. Me Me H SO₂ S 2417. Me Me H S SO₂ 2418. Me Me H SO SO₂ 2419. Me Me H SO₂ SO₂

TABLE 14 Inventive compounds of the general formula (I) in which Q is Q2, R⁵ is hydrogen and n is 2

No. R¹ R³ R⁴ X Y 1H NMR 2420. Me Me Me S C═O 2421. Me Me Me SO C═O 2422. Me Me Me SO₂ C═O 2423. Me Me Me S CHOMe 2424. Me Me Me SO CHOMe 2425. Me Me Me SO₂ CHOMe 2426. Me Me Me S CHOEt 2427. Me Me Me SO CHOEt 2428. Me Me Me SO₂ CHOEt 2429. Me Me Me S C═NOMe 2430. Me Me Me SO C═NOMe 2431. Me Me Me SO₂ C═NOMe 2432. Me Me Me S C═NOEt 2433. Me Me Me SO C═NOEt 2434. Me Me Me SO₂ C═NOEt 2435. Me Me Me S O 2436. Me Me Me SO O 2437. Me Me Me SO₂ O 2438. Me Me Me S S 2439. Me Me Me SO S 2440. Me Me Me SO₂ S 2441. Me Me Me S SO₂ 2442. Me Me Me SO SO₂ 2443. Me Me Me SO₂ SO₂ 2444. Me Me H S C═O 2445. Me Me H SO C═O 2446. Me Me H SO₂ C═O 2447. Me Me H S CHOMe 2448. Me Me H SO CHOMe 2449. Me Me H SO₂ CHOMe 2450. Me Me H S CHOEt 2451. Me Me H SO CHOEt 2452. Me Me H SO₂ CHOEt 2453. Me Me H S C═NOMe 2454. Me Me H SO C═NOMe 2455. Me Me H SO₂ C═NOMe 2456. Me Me H S C═NOEt 2457. Me Me H SO C═NOEt 2458. Me Me H SO₂ C═NOEt 2459. Me Me H S O 2460. Me Me H SO O 2461. Me Me H SO₂ O 2462. Me Me H S S 2463. Me Me H SO S 2464. Me Me H SO₂ S 2465. Me Me H S SO₂ 2466. Me Me H SO SO₂ 2467. Me Me H SO₂ SO₂

TABLE 15 Inventive compounds of the general formula (I) in which Q is Q3, R⁵ is hydrogen and n is 2

No. R¹ R³ R⁴ X Y 1H NMR 2468. Me Me Me S C═O 2469. Me Me Me SO C═O 2470. Me Me Me SO₂ C═O 2471. Me Me Me S CHOMe 2472. Me Me Me SO CHOMe 2473. Me Me Me SO₂ CHOMe 2474. Me Me Me S CHOEt 2475. Me Me Me SO CHOEt 2476. Me Me Me SO₂ CHOEt 2477. Me Me Me S C═NOMe 2478. Me Me Me SO C═NOMe 2479. Me Me Me SO₂ C═NOMe 2480. Me Me Me S C═NOEt 2481. Me Me Me SO C═NOEt 2482. Me Me Me SO₂ C═NOEt 2483. Me Me Me S O 2484. Me Me Me SO O 2485. Me Me Me SO₂ O 2486. Me Me Me S S 2487. Me Me Me SO S 2488. Me Me Me SO₂ S 2489. Me Me Me S SO₂ 2490. Me Me Me SO SO₂ 2491. Me Me Me SO₂ SO₂ 2492. Me Me H S C═O 2493. Me Me H SO C═O 2494. Me Me H SO₂ C═O 2495. Me Me H S CHOMe 2496. Me Me H SO CHOMe 2497. Me Me H SO₂ CHOMe 2498. Me Me H S CHOEt 2499. Me Me H SO CHOEt 2500. Me Me H SO₂ CHOEt 2501. Me Me H S C═NOMe 2502. Me Me H SO C═NOMe 2503. Me Me H SO₂ C═NOMe 2504. Me Me H S C═NOEt 2505. Me Me H SO C═NOEt 2506. Me Me H SO₂ C═NOEt 2507. Me Me H S O 2508. Me Me H SO O 2509. Me Me H SO₂ O 2510. Me Me H S S 2511. Me Me H SO S 2512. Me Me H SO₂ S 2513. Me Me H S SO₂ 2514. Me Me H SO SO₂ 2515. Me Me H SO₂ SO₂

B. FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a     compound of the formula (I) and/or a salt thereof and 90 parts by     weight of talc as an inert substance, and comminuting the mixture in     a hammer mill. -   b) A readily water-dispersible wettable powder is obtained by mixing     25 parts by weight of a compound of the formula (I) and/or salts     thereof, 64 parts by weight of kaolin-containing quartz as an inert     substance, 10 parts by weight of potassium lignosulfonate and 1 part     by weight of sodium oleylmethyltaurate as a wetting agent and     dispersant, and grinding the mixture in a pinned-disk mill. -   c) A readily water-dispersible dispersion concentrate is obtained by     mixing 20 parts by weight of a compound of the formula (I) and/or     salts thereof with 6 parts by weight of alkylphenol polyglycol ether     (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether     (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling     range for example about 255 to above 277° C.), and grinding the     mixture in a ball mill to a fineness of below 5 microns. -   d) An emulsifiable concentrate is obtained from 15 parts by weight     of a compound of the formula (I) and/or salts thereof, 75 parts by     weight of cyclohexanone as a solvent and 10 parts by weight of     ethoxylated nonylphenol as an emulsifier. -   e) Water-dispersible granules are obtained by mixing     -   75 parts by weight of a compound of the formula (I) and/or salts         thereof,     -   10 parts by weight of calcium lignosulfonate,     -   5 parts by weight of sodium laurylsulfate,     -   3 parts by weight of polyvinyl alcohol and     -   7 parts by weight of kaolin,     -   grinding the mixture in a pinned-disk mill and granulating the         powder in a fluidized bed by spraying on water as a granulating         liquid. -   f) Water-dispersible granules are also obtained by homogenizing and     precomminuting     -   25 parts by weight of a compound of the formula (I) and/or salts         thereof,     -   5 parts by weight of sodium         2,2′-dinaphthylmethane-6,6′-disulfonate,     -   2 parts by weight of sodium oleylmethyltaurate,     -   1 part by weight of polyvinyl alcohol,     -   17 parts by weight of calcium carbonate and     -   50 parts by weight of water     -   in a colloid mill, then grinding the mixture in a bead mill and         atomizing and drying the resulting suspension in a spray tower         by means of a one-substance nozzle.

C. BIOLOGICAL EXAMPLES 1. Pre-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in wood-fiber pots in sandy loam and covered with soil. The inventive compounds formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the covering soil as an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted) with addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the test plants. The damage to the test plants is assessed visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% action=the plants have died, 0% action=like control plants). For example, compounds No. 7, 9, 40, 187 and 189 at an application rate of 320 g/ha each show at least 80% efficacy against Abutilon theophrasti and Amaranthus retroflexus. Compounds No. 9, 40, 187, 189 and 2204 at an application rate of 320 g/ha each show at least 80% efficacy against Matricaria inodora, Stellaria media and Veronica persica.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants are placed in sandy loam in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The inventive compounds formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green parts of the plants as an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted) with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the formulations is scored visually in comparison to untreated controls (herbicidal action in percent (%): 100% action=the plants have died, 0% action=like control plants).

Examples of good post-emergence efficacy (PO). For example, compounds No. 7 and 2204 at an application rate of 80 g/ha each show at least 80% efficacy against Abutilon theophrasti and Viola tricolor. Compounds No. 9, 187 and 189 at an application rate of 80 g/ha each show at least 80% efficacy against Abutilon theophrasti and Amaranthus retroflexus. Compounds No. 40, 187 and 189 at an application rate of 80 g/ha each show at least 80% efficacy against Matricaria inodora, Stellaria media and Veronica Persica. 

1. An N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloarylcarboxamide of formula (I) and/or a salt thereof

in which Q is a Q1, Q2 or Q3 radical,

R¹ is (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₂-C₆)-alkenyl, (C₁-C₆)-alkoxy-(C₂-C₆)-alkynyl, CH₂R⁶, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by at least one u radical selected from the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl; R² is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy, halo-(C₂-C₆)-alkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or phenyl each substituted by at least one u radical selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen; R³ and R⁴ are each independently hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, (C₃-C₇)-halocycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro or cyano; R⁵ is hydrogen or fluorine; R⁶ is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C₃-C₆)-cycloalkyl, or heteroaryl, heterocyclyl or phenyl each substituted by at least one u radical selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen; R⁷ and R⁸ are each independently hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, halo-(C₃-C₇)-cycloalkyl, —OR⁹, S(O)_(m)R⁹, (C₁-C₆)-alkylthio, halo-(C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, halo-(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, halo-(C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro, cyano, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by at least one u radical selected from the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, or R⁷ and R⁸ together with the carbon atom to which they are bonded form the —X¹—(CH₂)_(r)—X²—, —(CH₂)_(s)—X³—, —(CH₂)_(t)—X³—CH₂—, —(CH₂)_(v)—X³—CH₂CH₂— or —(CH₂)_(w)— unit in which each of the (CH₂) groups is substituted by at least one m radical selected from the group consisting of halogen, methyl and (C₁-C₃)-alkoxy, or R⁷ and R⁸ together with the carbon atom to which they are bonded form the —O—N((C₁-C₃)-alkyl)-CHR¹⁰—CH₂— or —O—N═CR¹⁰—CH₂— unit in which each of the (CH₂) groups is substituted by at least one m radical selected from the group consisting of halogen and methyl; R⁹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, (C₃-C₇)-halocycloalkyl, (C₃-C₇)-cycloalkyl-(C₁-C₃)-alkyl, halo-(C₃-C₇)-cycloalkyl-(C₁-C₃)-alkyl, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by at least one s radical selected from the group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl; R¹⁰ is hydrogen, (C₁-C₃)-alkyl, or phenyl substituted by at least one u radical selected from the group consisting of (C₁-C₃)-alkyl, halogen, cyano and nitro; R¹¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, formyl, (C₂-C₆)-alkylcarbonyl, (C₂-C₆)-alkoxycarbonyl or (C₁-C₂)-alkylsulfonyl; X and Y are each independently O, S, SO, SO₂, C═O, C═S, NR¹⁰, CR⁷R⁸, C═NOR¹⁰ or C═NN(R¹¹)₂; X¹ and X² are each independently O, S or N((C₁-C₃)-alkyl); X³ is O or S; m is 0, 1 or 2; n is 1, 2 or 3; r is 2, 3 or 4; s is 2, 3, 4 or 5; t is 1, 2, 3 or 4; u is 0, 1, 2 or 3; v is 2 or 3; w is 2, 3, 4, 5 or
 6. 2. An N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloarylcarboxamide as claimed in claim 1, in which R¹ is (C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, halo-(C₁-C₃)-alkyl or (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl; R² is hydrogen, (C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, halo-(C₁-C₃)-alkyl, (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, methoxycarbonyl, ethoxycarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl or methoxymethyl; R³ and R⁴ are each independently hydrogen, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro or cyano; R⁵ is hydrogen; R⁷ and R⁸ are each independently hydrogen, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, —OR⁹, —S(O)_(m)R⁹, (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl, (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl, halogen, nitro, cyano, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by at least one u radical selected from the group consisting of halogen, nitro, cyano, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl, (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy and (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl, or R⁷ and R⁸ together with the carbon atom to which they are bonded form the —X¹—(CH₂)_(r)—X²—, —(CH₂)_(s)—X³—, —(CH₂)_(t)—X³—CH₂—, —(CH₂)_(v)—X³—CH₂CH₂— or —(CH₂)_(w)— unit in which each of the (CH₂) groups is substituted by at least one m radical selected from the group consisting of halogen, methyl and (C₁-C₃)-alkoxy, or R⁷ and R⁸ together with the carbon atom to which they are bonded form the —O—N((C₁-C₃)-alkyl)-CHR¹⁰—CH₂— or —O—N═CR¹⁰—CH₂— unit in which each of the (CH₂) groups is substituted by at least one m radical selected from the group consisting of halogen and methyl; R⁹ is hydrogen, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₂-C₃)-alkenyl, (C₂-C₄)-alkynyl, (C₃-C₅)-cycloalkyl, (C₃-C₅)-cycloalkyl-(C₁-C₃)-alkyl, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by at least one s radical selected from the group consisting of halogen, nitro, cyano, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl, (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy and (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl; R¹⁰ is hydrogen or (C₁-C₃)-alkyl; X and Y are each independently O, SO₂, C═O, C═S, CR⁷R⁸, C═NOR¹⁰; X¹ and X² are each independently O, S, N(CH₃); X³ is O or S; m is 0, 1 or 2; n is 1 or 2; r is 2 or 3; s is 2, 3 or 4; t is 1, 2 or 3; u is 0, 1 or 2; v is 2 or 3; w is 2, 3, 4 or
 5. 3. A herbicidal composition, comprising a herbicidally active content of at least one compound of formula (I) as claimed in claim
 1. 4. The herbicidal composition as claimed in claim 3 in a mixture with at least one formulation auxiliary.
 5. A herbicidal composition as claimed in claim 3, comprising at least one further pesticidally active substance selected from the group consisting of an insecticide, an acaricide, a herbicide, a fungicide, a safener and a growth regulator.
 6. The herbicidal composition as claimed in claim 5, comprising a safener.
 7. A herbicidal composition as claimed in claim 6, comprising a cyprosulfamide, a cloquintocet-mexyl, a mefenpyr-diethyl and/or a isoxadifen-ethyl.
 8. A herbicidal composition as claimed in claim 5, comprising a further herbicide.
 9. A method for controlling an unwanted plant, comprising applying an effective amount of at least one compound of formula (I) and/or salt thereof as claimed in claim 1, to a plant and/or a site of unwanted vegetation.
 10. The compound of formula (I) and/or salt thereof as claimed in claim 1, capable of being used for controlling an unwanted plant.
 11. The compound of formula (I) and/or salt thereof as claimed in claim 10, wherein said compound of formula (I) is capable of being used for controlling an unwanted plant in a crop of a useful plant.
 12. The compound of formula (I) capable of being used as claimed in claim 11, wherein the useful plant is a transgenic useful plant.
 13. A method for controlling an unwanted plant, comprising applying an effective amount of at least one compound of formula (I) and/or salt thereof as claimed in claim 2, to a plant and/or to a site of unwanted vegetation.
 14. A method for controlling an unwanted plant, comprising applying an effective amount of a herbicidal composition as claimed in claim 3, to a plant and/or to a site of unwanted vegetation.
 15. The compound of formula (I) and/or salt thereof as claimed in claim 2, capable of being used for controlling an unwanted plant.
 16. A herbicidal composition as claimed in claim 3 capable of being used for controlling an unwanted plant. 